dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bd2c3a09eb4440ea9b796c43f188c4cb | CCOCC(=O)Cl.Cc1nc(Oc2ccccc2)c(N)c(NCCCCNC(=O)OC(C)(C)C)c1C>>CCOCC(=O)Nc1c(Oc2ccccc2)nc(C)c(C)c1NCCCCNC(=O)OC(C)(C)C | C(C)N(CC)CC.NC=1C(=NC(=C(C1NCCCCNC(OC(C)(C)C)=O)C)C)OC1=CC=CC=C1.C(C)OCC(=O)Cl>>C(C)OCC(=O)NC=1C(=NC(=C(C1NCCCCNC(OC(C)(C)C)=O)C)C)OC1=CC=CC=C1 | Cl[C:5]([CH2:4][O:3][CH2:2][CH3:1])=[O:6].[NH2:7][c:8]1[c:9]([O:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[n:17][c:18]([CH3:19])[c:20]([CH3:21])[c:22]1[NH:23][CH2:24][CH2:25][CH2:26][CH2:27][NH:28][C:29](=[O:30])[O:31][C:32]([CH3:33])([CH3:34])[CH3:35]>>[CH3:1][CH2:2][O:3][CH2:4][C:5](=[O:6])[NH:7][c:8]1[c:9]([O:1... | CCOCC(=O)Cl.Cc1nc(Oc2ccccc2)c(N)c(NCCCCNC(=O)OC(C)(C)C)c1C | CCOCC(=O)Nc1c(Oc2ccccc2)nc(C)c(C)c1NCCCCNC(=O)OC(C)(C)C | null | null | ClCCl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccc(Oc2ccccn2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#8:4].[#8:5]-[c:6](:[#7;a:7]:[c:8]):[c:9](-[NH2;D1;+0:10]):[c:11]>>[#8:5]-[c:6](:[#7;a:7]:[c:8]):[c:9](-[NH;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#8:4]):[c:11] | null | [] | null | null | 1 | HOUR | Triethylamine (3.3 mL, 23.7 mmol) was added to a chilled (0° C.) mixture of tert-butyl 4-[(3-amino-5,6-dimethyl-2-phenoxypyridin-4-yl)amino]butylcarbamate (8.60 g, 21.5 mmol) and anhydrous dichloromethane (200 mL). Ethoxyacetyl chloride (2.76 g, 22.5 mmol) was added. After one hour the reaction mixture was allowed to w... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccncc1.c1ccccc1 | HCl | ClCCl | null | 1 | CCOCC(=O)Cl.Cc1nc(Oc2ccccc2)c(N)c(NCCCCNC(=O)OC(C)(C)C)c1C>ClCCl>CCOCC(=O)Nc1c(Oc2ccccc2)nc(C)c(C)c1NCCCCNC(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-af830e802a4a4f1a9c5d4fc11eea550d | CCCCc1nc2c(Oc3ccccc3)nc(C)c(C)c2n1CCCCN.CN(C)CCOC(c1ccccc1)c1ccc(C(=O)Cl)cc1>>CCCCc1nc2c(Oc3ccccc3)nc(C)c(C)c2n1CCCCNC(=O)c1ccc(C(OCCN(C)C)c2ccccc2)cc1 | C(CCC)C=1N(C2=C(C(=NC(=C2C)C)OC2=CC=CC=C2)N1)CCCCN.C(C)N(CC)CC.CN(CCOC(C1=CC=C(C(=O)Cl)C=C1)C1=CC=CC=C1)C>>C(CCC)C=1N(C2=C(C(=NC(=C2C)C)OC2=CC=CC=C2)N1)CCCCNC(C1=CC=C(C=C1)C(C1=CC=CC=C1)OCCN(C)C)=O | [CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([O:9][c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)[n:16][c:17]([CH3:18])[c:19]([CH3:20])[c:21]2[n:22]1[CH2:23][CH2:24][CH2:25][CH2:26][NH2:27].Cl[C:28](=[O:29])[c:30]1[cH:31][cH:32][c:33]([CH:34]([O:35][CH2:36][CH2:37][N:38]([CH3:39])[CH3:40])[c:41]2[cH:42][cH:43][cH:44... | CCCCc1nc2c(Oc3ccccc3)nc(C)c(C)c2n1CCCCN.CN(C)CCOC(c1ccccc1)c1ccc(C(=O)Cl)cc1 | CCCCc1nc2c(Oc3ccccc3)nc(C)c(C)c2n1CCCCNC(=O)c1ccc(C(OCCN(C)C)c2ccccc2)cc1 | null | null | ClCCl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NCCCCn1cnc2c(Oc3ccccc3)nccc21)c1ccc(Cc2ccccc2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 47.2 | [{"value": 47.2, "product": "C(CCC)C=1N(C2=C(C(=NC(=C2C)C)OC2=CC=CC=C2)N1)CCCCNC(C1=CC=C(C=C1)C(C1=CC=CC=C1)OCCN(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | Under a nitrogen atmosphere, 4-(2-butyl-6,7-dimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl)butan-1-amine (122 mg, 0.33 mmol) was dissolved in dichloromethane and triethylamine (0.093 mL, 0.67 mmol). The solution was cooled in an ice-water bath and 4-[[2-(dimethylamino)ethoxy](phenyl)methyl]benzoyl chloride (106 mg, 0... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1cc2nc[nH]c2cn1.c1ccccc1.c1ccccc1 | HCl | ClCCl | null | 16 | CCCCc1nc2c(Oc3ccccc3)nc(C)c(C)c2n1CCCCN.CN(C)CCOC(c1ccccc1)c1ccc(C(=O)Cl)cc1>ClCCl>CCCCc1nc2c(Oc3ccccc3)nc(C)c(C)c2n1CCCCNC(=O)c1ccc(C(OCCN(C)C)c2ccccc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-87c9ff738a5e4092aff5b199968a09bd | CCCCc1nc2c(Oc3ccccc3)nc(C)c(C)c2n1CCCCNC(=O)c1ccc(C(OCCN(C)C)c2ccccc2)cc1.[NH4+]>>CCCCc1nc2c(N)nc(C)c(C)c2n1CCCCNC(=O)c1ccc(C(OCCN(C)C)c2ccccc2)cc1 | C(CCC)C=1N(C2=C(C(=NC(=C2C)C)OC2=CC=CC=C2)N1)CCCCNC(C1=CC=C(C=C1)C(C1=CC=CC=C1)OCCN(C)C)=O.C(C)(=O)[O-].[NH4+].[OH-].[Na+]>>NC1=NC(=C(C2=C1N=C(N2CCCCNC(C2=CC=C(C=C2)C(C2=CC=CC=C2)OCCN(C)C)=O)CCCC)C)C | c1ccc(O[c:8]2[c:7]3[n:6][c:5]([CH2:4][CH2:3][CH2:2][CH3:1])[n:16]([CH2:17][CH2:18][CH2:19][CH2:20][NH:21][C:22](=[O:23])[c:24]4[cH:25][cH:26][c:27]([CH:28]([O:29][CH2:30][CH2:31][N:32]([CH3:33])[CH3:34])[c:35]5[cH:36][cH:37][cH:38][cH:39][cH:40]5)[cH:41][cH:42]4)[c:15]3[c:13]([CH3:14])[c:11]([CH3:12])[n:10]2)cc1.[NH4+:... | CCCCc1nc2c(Oc3ccccc3)nc(C)c(C)c2n1CCCCNC(=O)c1ccc(C(OCCN(C)C)c2ccccc2)cc1.[NH4+] | CCCCc1nc2c(N)nc(C)c(C)c2n1CCCCNC(=O)c1ccc(C(OCCN(C)C)c2ccccc2)cc1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | f1a3cc602ce132f4b138aaff43e359cc4e4ed2f1a7bdd06ecc27d202417b41fd | 4764b8d6a7ad8d9253070fdb827f95d720ac9a4f642f3b03b75fe3f308c3d0a7 | O=C(NCCCCn1cnc2cnccc21)c1ccc(Cc2ccccc2)cc1 | [C:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]2:[c:6]:1:[c:7]:[c:8]:[#7;a:9]:[c;H0;D3;+0:10]:2-O-c1:c:c:c:c:c:1.[NH4+;D0:11]>>[C:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]2:[c:6]:1:[c:7]:[c:8]:[#7;a:9]:[c;H0;D3;+0:10]:2-[NH2;D1;+0:11] | 15.3 | [{"value": 15.3, "product": "NC1=NC(=C(C2=C1N=C(N2CCCCNC(C2=CC=C(C=C2)C(C2=CC=CC=C2)OCCN(C)C)=O)CCCC)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 150 | CELSIUS | null | null | N-[4-(2-Butyl-6,7-dimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-4-[[2-(dimethylamino)ethoxy](phenyl)methyl]benzamide (101 mg, 0.16 mmol) and ammonium acetate (1.1 g) were placed into a pressure tube along with a stir bar. The tube was sealed and heated at 150° C. for 16 hours. The reaction was cooled to room ... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Primary amine | c1ccccc1.c1cc2nc[nH]c2cn1 | c1cc2nc[nH]c2cn1 | c1cc2nc[nH]c2cn1.c1ccccc1.c1ccccc1 | HO- | O | 150 | null | CCCCc1nc2c(Oc3ccccc3)nc(C)c(C)c2n1CCCCNC(=O)c1ccc(C(OCCN(C)C)c2ccccc2)cc1.[NH4+]>O>CCCCc1nc2c(N)nc(C)c(C)c2n1CCCCNC(=O)c1ccc(C(OCCN(C)C)c2ccccc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fded4986a54d42f184599c02d1ee8017 | CC(C)(C)OC(=O)NCCCCN.Cc1cc(Cl)c([N+](=O)[O-])c(Cl)n1>>Cc1cc(NCCCCNC(=O)OC(C)(C)C)c([N+](=O)[O-])c(Cl)n1 | NCCCCNC(OC(C)(C)C)=O.ClC1=NC(=CC(=C1[N+](=O)[O-])Cl)C>>ClC1=NC(=CC(=C1[N+](=O)[O-])NCCCCNC(OC(C)(C)C)=O)C | [NH2:5][CH2:6][CH2:7][CH2:8][CH2:9][NH:10][C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17].Cl[c:4]1[cH:3][c:2]([CH3:1])[n:24][c:22]([Cl:23])[c:18]1[N+:19](=[O:20])[O-:21]>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][CH2:6][CH2:7][CH2:8][CH2:9][NH:10][C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[c:18]([N+:19](=[O:... | CC(C)(C)OC(=O)NCCCCN.Cc1cc(Cl)c([N+](=O)[O-])c(Cl)n1 | Cc1cc(NCCCCNC(=O)OC(C)(C)C)c([N+](=O)[O-])c(Cl)n1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccncc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[C;D1;H3:4]):[#7;a:5]:[c:6](-[Cl;D1;H0:7]):[c:8]:1-[#7;+:9].[C:10]-[C:11]-[NH2;D1;+0:12]>>[#7;+:9]-[c:8]1:[c:6](-[Cl;D1;H0:7]):[#7;a:5]:[c:3](-[C;D1;H3:4]):[c:2]:[c;H0;D3;+0:1]:1-[NH;D2;+0:12]-[C:11]-[C:10] | 98.5 | [{"value": 98.5, "product": "ClC1=NC(=CC(=C1[N+](=O)[O-])NCCCCNC(OC(C)(C)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of tert-butyl 4-aminobutylcarbamate (32.12 g, 170.6 mmol) in N,N-dimethylformamide (200 mL) was added over a period of 90 minutes to a solution of 2,4-dichloro-6-methyl-3-nitropyridine (35.09 g, 169.5 mmol) in N,N-dimethylformamide (500 mL). The reaction mixture was stirred at ambient temperature overnight. ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1 | HCl | CN(C=O)C | null | 8 | CC(C)(C)OC(=O)NCCCCN.Cc1cc(Cl)c([N+](=O)[O-])c(Cl)n1>CN(C=O)C>Cc1cc(NCCCCNC(=O)OC(C)(C)C)c([N+](=O)[O-])c(Cl)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-50ec6fbfd98d4be997fd1a0e11cd3c83 | Cc1cc(NCCCCNC(=O)OC(C)(C)C)c([N+](=O)[O-])c(Cl)n1.Oc1ccccc1>>Cc1cc(NCCCCNC(=O)OC(C)(C)C)c([N+](=O)[O-])c(Oc2ccccc2)n1 | ClC1=NC(=CC(=C1[N+](=O)[O-])NCCCCNC(OC(C)(C)C)=O)C.C1(=CC=CC=C1)O.[H-].[Na+]>>CC1=CC(=C(C(=N1)OC1=CC=CC=C1)[N+](=O)[O-])NCCCCNC(OC(C)(C)C)=O | Cl[c:22]1[c:18]([N+:19](=[O:20])[O-:21])[c:4]([NH:5][CH2:6][CH2:7][CH2:8][CH2:9][NH:10][C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[cH:3][c:2]([CH3:1])[n:30]1.[OH:23][c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][CH2:6][CH2:7][CH2:8][CH2:9][NH:10][C:11](=[O:12])[O:13][C:14]([CH... | Cc1cc(NCCCCNC(=O)OC(C)(C)C)c([N+](=O)[O-])c(Cl)n1.Oc1ccccc1 | Cc1cc(NCCCCNC(=O)OC(C)(C)C)c([N+](=O)[O-])c(Oc2ccccc2)n1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 99925b30dd2603ae575cba81b58435d015cd6b7267cf347380904f25833af5f2 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(Oc2ccccn2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10]):[#7;a:2]:[c:3] | 64.5 | [{"value": 64.5, "product": "CC1=CC(=C(C(=N1)OC1=CC=CC=C1)[N+](=O)[O-])NCCCCNC(OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | Phenol (9.45 g, 100 mmol) was added over a period of 10 minutes to a chilled (0° C.) suspension of sodium hydride (4.24 g of 60%, 106 mmol) in anhydrous tetrahydrofuran (100 mL). The reaction mixture was allowed to stir at 0° C. for 30 minutes. A solution of tert-butyl 4-[(2-chloro-6-methyl-3-nitropyridin-4-yl)amino]bu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccccc1 | HCl | O1CCCC1 | 0 | 0.5 | Cc1cc(NCCCCNC(=O)OC(C)(C)C)c([N+](=O)[O-])c(Cl)n1.Oc1ccccc1>O1CCCC1>Cc1cc(NCCCCNC(=O)OC(C)(C)C)c([N+](=O)[O-])c(Oc2ccccc2)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-48da2f105fed42b28ddfbc3e3e09c3ab | CC(C)C(=O)Cl.CCOCc1nc2c(N)nc(C)cc2n1CCCCN>>CCOCc1nc2c(N)nc(C)cc2n1CCCCNC(=O)C(C)C | C(C(C)C)(=O)Cl.NCCCCN1C(=NC=2C(=NC(=CC21)C)N)COCC.C(C)N(CC)CC>>NC1=NC(=CC2=C1N=C(N2CCCCNC(C(C)C)=O)COCC)C | Cl[C:21](=[O:22])[CH:23]([CH3:24])[CH3:25].[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]([CH3:12])[cH:13][c:14]2[n:15]1[CH2:16][CH2:17][CH2:18][CH2:19][NH2:20]>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]([CH3:12])[cH:13][c:14]2[n:15]1[CH2:16][CH2:17][CH2:18][CH2:19][NH... | CC(C)C(=O)Cl.CCOCc1nc2c(N)nc(C)cc2n1CCCCN | CCOCc1nc2c(N)nc(C)cc2n1CCCCNC(=O)C(C)C | null | null | C(Cl)(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1cc2[nH]cnc2cn1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[C;D1;H3:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[C;D1;H3:5] | 41.2 | [{"value": 41.2, "product": "NC1=NC(=CC2=C1N=C(N2CCCCNC(C(C)C)=O)COCC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | Isobutyryl chloride (181 μL, 1.73 mmol) was added to a solution of 1-(4-aminobutyl)-2-ethoxymethyl-6-methyl-1H-imidazo[4,5-c]pyridin-4-amine (0.435 g, 1.57 mmol), triethylamine (280 μL, 2.04 mmol) and chloroform (8 mL). The reaction mixture was allowed to stir at ambient temperature for 4 hours then it was diluted with... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1cc2nc[nH]c2cn1 | HCl | C(Cl)(Cl)Cl | null | 4 | CC(C)C(=O)Cl.CCOCc1nc2c(N)nc(C)cc2n1CCCCN>C(Cl)(Cl)Cl>CCOCc1nc2c(N)nc(C)cc2n1CCCCNC(=O)C(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-70c165635d014dcb99ca60dfce845323 | CC(C)(C)OC(=O)NCCCCN.Cc1nc(Cl)c([N+](=O)[O-])c(Cl)c1C>>Cc1nc(Cl)c([N+](=O)[O-])c(NCCCCNC(=O)OC(C)(C)C)c1C | NCCCCNC(OC(C)(C)C)=O.ClC1=NC(=C(C(=C1[N+](=O)[O-])Cl)C)C.C(C)N(CC)CC>>ClC1=NC(=C(C(=C1[N+](=O)[O-])NCCCCNC(OC(C)(C)C)=O)C)C | [NH2:11][CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23].Cl[c:10]1[c:6]([N+:7](=[O:8])[O-:9])[c:4]([Cl:5])[n:3][c:2]([CH3:1])[c:24]1[CH3:25]>>[CH3:1][c:2]1[n:3][c:4]([Cl:5])[c:6]([N+:7](=[O:8])[O-:9])[c:10]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17](=[O:18])[O:19]... | CC(C)(C)OC(=O)NCCCCN.Cc1nc(Cl)c([N+](=O)[O-])c(Cl)c1C | Cc1nc(Cl)c([N+](=O)[O-])c(NCCCCNC(=O)OC(C)(C)C)c1C | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccncc1 | Cl-[c;H0;D3;+0:1]1:[c:2](-[C;D1;H3:3]):[c:4](-[C;D1;H3:5]):[#7;a:6]:[c:7](-[Cl;D1;H0:8]):[c:9]:1-[#7;+:10].[C:11]-[C:12]-[NH2;D1;+0:13]>>[#7;+:10]-[c:9]1:[c:7](-[Cl;D1;H0:8]):[#7;a:6]:[c:4](-[C;D1;H3:5]):[c:2](-[C;D1;H3:3]):[c;H0;D3;+0:1]:1-[NH;D2;+0:13]-[C:12]-[C:11] | 48 | [{"value": 48.0, "product": "ClC1=NC(=C(C(=C1[N+](=O)[O-])NCCCCNC(OC(C)(C)C)=O)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of tert-butyl 4-aminobutylcarbamate (8.52 g, 45.24 mmol) in N,N-dimethylformamide was added to a solution of 2,4-dichloro-5,6-dimethyl-3-nitropyridine (10.00 g, 45.24 mmol) and triethylamine (12.6 mL, 90.5 mmol) in N,N-dimethylformamide (320 mL). The reaction mixture was stirred overnight and then concentrat... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1 | HCl | CN(C=O)C | null | 8 | CC(C)(C)OC(=O)NCCCCN.Cc1nc(Cl)c([N+](=O)[O-])c(Cl)c1C>CN(C=O)C>Cc1nc(Cl)c([N+](=O)[O-])c(NCCCCNC(=O)OC(C)(C)C)c1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6c5a2790c19e40d4a7d7b2c554a8b2c2 | Cc1nc(Oc2ccccc2)c([N+](=O)[O-])c(NCCCCNC(=O)OC(C)(C)C)c1C>>Cc1nc(Oc2ccccc2)c(N)c(NCCCCNC(=O)OC(C)(C)C)c1C | CC1=NC(=C(C(=C1C)NCCCCNC(OC(C)(C)C)=O)[N+](=O)[O-])OC1=CC=CC=C1>>NC=1C(=NC(=C(C1NCCCCNC(OC(C)(C)C)=O)C)C)OC1=CC=CC=C1 | O=[N+:13]([O-])[c:12]1[c:4]([O:5][c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[n:3][c:2]([CH3:1])[c:28]([CH3:29])[c:14]1[NH:15][CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27]>>[CH3:1][c:2]1[n:3][c:4]([O:5][c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[c:12]([NH2:13])[c:14]([NH:15][CH... | Cc1nc(Oc2ccccc2)c([N+](=O)[O-])c(NCCCCNC(=O)OC(C)(C)C)c1C | Cc1nc(Oc2ccccc2)c(N)c(NCCCCNC(=O)OC(C)(C)C)c1C | null | [Pd] | C(C)(C)O.C1(=CC=CC=C1)C | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(Oc2ccccn2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4](-[#8:5]):[#7;a:6]:[c:7]>>[#8:5]-[c:4](:[#7;a:6]:[c:7]):[c:2](-[NH2;D1;+0:1]):[c:3] | 90.6 | [{"value": 90.6, "product": "NC=1C(=NC(=C(C1NCCCCNC(OC(C)(C)C)=O)C)C)OC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of tert-butyl 4-[(2,3-dimethyl-5-nitro-6-phenoxypyridin-4-yl)amino]butylcarbamate (7.32 g, 17.00 mmol) in a mixture of toluene (150 mL) and isopropanol (10 mL) was combined with a slurry of 10% palladium on carbon in toluene. The mixture was place under hydrogen pressure on a Parr apparatus for 24 hours. Add... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccncc1.c1ccccc1 | Other | [Pd].C(C)(C)O.C1(=CC=CC=C1)C | null | null | Cc1nc(Oc2ccccc2)c([N+](=O)[O-])c(NCCCCNC(=O)OC(C)(C)C)c1C>[Pd].C(C)(C)O.C1(=CC=CC=C1)C>Cc1nc(Oc2ccccc2)c(N)c(NCCCCNC(=O)OC(C)(C)C)c1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-744573d22e094a1085efd4fa62a9a1fb | CC(=O)NCCCCn1cnc2c(N)nc(C)c(C)c21>>Cc1nc(N)c2ncn(CCCCN)c2c1C | NC1=NC(=C(C2=C1N=CN2CCCCNC(C)=O)C)C>>NCCCCN1C=NC=2C(=NC(=C(C21)C)C)N | CC(=O)[NH:14][CH2:13][CH2:12][CH2:11][CH2:10][n:9]1[cH:8][n:7][c:6]2[c:4]([NH2:5])[n:3][c:2]([CH3:1])[c:16]([CH3:17])[c:15]21>>[CH3:1][c:2]1[n:3][c:4]([NH2:5])[c:6]2[n:7][cH:8][n:9]([CH2:10][CH2:11][CH2:12][CH2:13][NH2:14])[c:15]2[c:16]1[CH3:17] | CC(=O)NCCCCn1cnc2c(N)nc(C)c(C)c21 | Cc1nc(N)c2ncn(CCCCN)c2c1C | null | null | Cl | Reduction | Hydrogenolysis of amides/imides/carbamates | 755df58c254dea764fdda078ffd678ec540bba057c83683be04c253f1270ac7b | 025f7cefe51e71668ad5d09fca32df168e9b538347403e4d5c1748073e538adc | c1cc2[nH]cnc2cn1 | C-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | 80.9 | [{"value": 80.9, "product": "NCCCCN1C=NC=2C(=NC(=C(C21)C)C)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | A solution of N-[4-(4-amino-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]acetamide (˜2.1 g) in 6 N hydrochloric acid (30 mL) was sealed in a flask and then heated at 100° C. for about 30 hours. The reaction mixture was allowed to cool to ambient temperature and then filtered to remove any particulates. The filtrate... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Primary amine | null | null | c1cc2nc[nH]c2cn1 | HO- | Cl | 100 | null | CC(=O)NCCCCn1cnc2c(N)nc(C)c(C)c21>Cl>Cc1nc(N)c2ncn(CCCCN)c2c1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0ffe6b5de4da45809dc6e19496796e1f | Cc1nc(Cl)c([N+](=O)[O-])c(Cl)c1C.NCCC1CCN(Cc2ccccc2)CC1>>Cc1nc(Cl)c([N+](=O)[O-])c(NCCC2CCN(Cc3ccccc3)CC2)c1C | NCCC1CCN(CC1)CC1=CC=CC=C1.ClC1=NC(=C(C(=C1[N+](=O)[O-])Cl)C)C.C(C)N(CC)CC>>C(C1=CC=CC=C1)N1CCC(CC1)CCNC1=C(C(=NC(=C1C)C)Cl)[N+](=O)[O-] | Cl[c:10]1[c:6]([N+:7](=[O:8])[O-:9])[c:4]([Cl:5])[n:3][c:2]([CH3:1])[c:27]1[CH3:28].[NH2:11][CH2:12][CH2:13][CH:14]1[CH2:15][CH2:16][N:17]([CH2:18][c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[CH2:25][CH2:26]1>>[CH3:1][c:2]1[n:3][c:4]([Cl:5])[c:6]([N+:7](=[O:8])[O-:9])[c:10]([NH:11][CH2:12][CH2:13][CH:14]2[CH2:15][CH2:1... | Cc1nc(Cl)c([N+](=O)[O-])c(Cl)c1C.NCCC1CCN(Cc2ccccc2)CC1 | Cc1nc(Cl)c([N+](=O)[O-])c(NCCC2CCN(Cc3ccccc3)CC2)c1C | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CN2CCC(CCNc3ccncc3)CC2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2](-[C;D1;H3:3]):[c:4](-[C;D1;H3:5]):[#7;a:6]:[c:7](-[Cl;D1;H0:8]):[c:9]:1-[#7;+:10].[C:11]-[C:12]-[NH2;D1;+0:13]>>[#7;+:10]-[c:9]1:[c:7](-[Cl;D1;H0:8]):[#7;a:6]:[c:4](-[C;D1;H3:5]):[c:2](-[C;D1;H3:3]):[c;H0;D3;+0:1]:1-[NH;D2;+0:13]-[C:12]-[C:11] | 60.4 | [{"value": 60.4, "product": "C(C1=CC=CC=C1)N1CCC(CC1)CCNC1=C(C(=NC(=C1C)C)Cl)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | HOUR | A solution of 4-(2-aminoethyl)-1-benzylpiperidine (9.88 g, 45.2 mmol) in N,N-dimethylformamide was added dropwise to a solution of 2,4-dichloro-5,6-dimethyl-3-nitropyridine (10.00 g, 45.2 mmol) and triethylamine (12.6 mL, 90.5 mmol) in N,N-dimethylformamide (320 mL). The reaction mixture was allowed to stir at ambient ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.C1CC[NH]CC1.c1ccccc1 | HCl | CN(C=O)C | null | 20 | Cc1nc(Cl)c([N+](=O)[O-])c(Cl)c1C.NCCC1CCN(Cc2ccccc2)CC1>CN(C=O)C>Cc1nc(Cl)c([N+](=O)[O-])c(NCCC2CCN(Cc3ccccc3)CC2)c1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a6816e427d124a9db3a59be7d7b22bd5 | Cc1nc(Cl)c([N+](=O)[O-])c(NCCC2CCN(Cc3ccccc3)CC2)c1C.Oc1ccccc1>>Cc1nc(Oc2ccccc2)c([N+](=O)[O-])c(NCCC2CCN(Cc3ccccc3)CC2)c1C | [H-].[Na+].C1(=CC=CC=C1)O.C(C1=CC=CC=C1)N1CCC(CC1)CCNC1=C(C(=NC(=C1C)C)Cl)[N+](=O)[O-].[O-]C1=CC=CC=C1>>C(C1=CC=CC=C1)N1CCC(CC1)CCNC1=C(C(=NC(=C1[N+](=O)[O-])OC1=CC=CC=C1)C)C | Cl[c:4]1[n:3][c:2]([CH3:1])[c:33]([CH3:34])[c:16]([NH:17][CH2:18][CH2:19][CH:20]2[CH2:21][CH2:22][N:23]([CH2:24][c:25]3[cH:26][cH:27][cH:28][cH:29][cH:30]3)[CH2:31][CH2:32]2)[c:12]1[N+:13](=[O:14])[O-:15].[OH:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1>>[CH3:1][c:2]1[n:3][c:4]([O:5][c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2... | Cc1nc(Cl)c([N+](=O)[O-])c(NCCC2CCN(Cc3ccccc3)CC2)c1C.Oc1ccccc1 | Cc1nc(Oc2ccccc2)c([N+](=O)[O-])c(NCCC2CCN(Cc3ccccc3)CC2)c1C | null | null | COCCOCCOC | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 99925b30dd2603ae575cba81b58435d015cd6b7267cf347380904f25833af5f2 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(CN2CCC(CCNc3ccnc(Oc4ccccc4)c3)CC2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10]):[#7;a:2]:[c:3] | 47.2 | [{"value": 47.2, "product": "C(C1=CC=CC=C1)N1CCC(CC1)CCNC1=C(C(=NC(=C1[N+](=O)[O-])OC1=CC=CC=C1)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | Sodium hydride (1.196 g of 60%, 29.9 mmol) was added to a solution of phenol (2.81 g, 29.9 mol) in diglyme (40 mL). The mixture was stirred for 15 minutes after the cessation of gas evolution. A solution of N-[2-(1-benzylpiperidin-4-yl)ethyl]-2-chloro-5,6-dimethyl-3-nitropyridin-4-amine (10.9 g, 27.2 mmol) in hot digly... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccccc1.C1CC[NH]CC1.c1ccccc1 | HCl | COCCOCCOC | null | 0.25 | Cc1nc(Cl)c([N+](=O)[O-])c(NCCC2CCN(Cc3ccccc3)CC2)c1C.Oc1ccccc1>COCCOCCOC>Cc1nc(Oc2ccccc2)c([N+](=O)[O-])c(NCCC2CCN(Cc3ccccc3)CC2)c1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-67c525531e714f879208c3e2898b9bcc | CC(C)C(=O)Cl.CCOCc1nc2c(N)nc(C)c(C)c2n1CCC1CCNCC1>>CCOCc1nc2c(N)nc(C)c(C)c2n1CCC1CCN(C(=O)C(C)C)CC1 | C(C(C)C)(=O)Cl.C(C)OCC=1N(C2=C(C(=NC(=C2C)C)N)N1)CCC1CCNCC1>>C(C)OCC=1N(C2=C(C(=NC(=C2C)C)N)N1)CCC1CCN(CC1)C(C(C)C)=O | Cl[C:23](=[O:24])[CH:25]([CH3:26])[CH3:27].[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]([CH3:12])[c:13]([CH3:14])[c:15]2[n:16]1[CH2:17][CH2:18][CH:19]1[CH2:20][CH2:21][NH:22][CH2:28][CH2:29]1>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]([CH3:12])[c:13]([CH3:14])[c:15]2... | CC(C)C(=O)Cl.CCOCc1nc2c(N)nc(C)c(C)c2n1CCC1CCNCC1 | CCOCc1nc2c(N)nc(C)c(C)c2n1CCC1CCN(C(=O)C(C)C)CC1 | null | null | ClCCl.C(Cl)(Cl)Cl | Acylation | N-alkylation of secondary amines with alkyl halides | aaa7c80569e6aa145ac8d7318e06893ee71aff0c965e85eca836522c948938d5 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | c1cc2c(cn1)ncn2CCC1CCNCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[C;D1;H3:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[C;D1;H3:5])-[C:9]-[C:10] | 50.2 | [{"value": 50.2, "product": "C(C)OCC=1N(C2=C(C(=NC(=C2C)C)N)N1)CCC1CCN(CC1)C(C(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Isobutyryl chloride (96 μL, 0.917 mmol) was added drop wise to a chilled (0° C.) solution of 2-(ethoxymethyl)-6,7-dimethyl-1-(2-piperidin-4-ylethyl)-1H-imidazo[4,5-c]pyridin-4-amine (304 mg, 0.917 mmol) in dichloromethane (10 mL). The reaction mixture was allowed to stir overnight then it was diluted with chloroform an... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | C1CCNCC1 | C1CC[NH]CC1 | c1cc2nc[nH]c2cn1.C1CC[NH]CC1 | HCl | ClCCl.C(Cl)(Cl)Cl | null | 8 | CC(C)C(=O)Cl.CCOCc1nc2c(N)nc(C)c(C)c2n1CCC1CCNCC1>ClCCl.C(Cl)(Cl)Cl>CCOCc1nc2c(N)nc(C)c(C)c2n1CCC1CCN(C(=O)C(C)C)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-48af6048d9f14699baeecd54e5333864 | CC(C)(C)OC(=O)NCCCN.Cc1nc(Cl)c([N+](=O)[O-])c(Cl)c1C>>Cc1nc(Cl)c([N+](=O)[O-])c(NCCCNC(=O)OC(C)(C)C)c1C | C(N)([O-])=O.NCCCNC(OC(C)(C)C)=O.ClC1=NC(=C(C(=C1[N+](=O)[O-])Cl)C)C.C(C)N(CC)CC>>ClC1=NC(=C(C(=C1[N+](=O)[O-])NCCCNC(OC(C)(C)C)=O)C)C | [NH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22].Cl[c:10]1[c:6]([N+:7](=[O:8])[O-:9])[c:4]([Cl:5])[n:3][c:2]([CH3:1])[c:23]1[CH3:24]>>[CH3:1][c:2]1[n:3][c:4]([Cl:5])[c:6]([N+:7](=[O:8])[O-:9])[c:10]([NH:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:17])[O:18][C:19]([CH3:20])... | CC(C)(C)OC(=O)NCCCN.Cc1nc(Cl)c([N+](=O)[O-])c(Cl)c1C | Cc1nc(Cl)c([N+](=O)[O-])c(NCCCNC(=O)OC(C)(C)C)c1C | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccncc1 | Cl-[c;H0;D3;+0:1]1:[c:2](-[C;D1;H3:3]):[c:4](-[C;D1;H3:5]):[#7;a:6]:[c:7](-[Cl;D1;H0:8]):[c:9]:1-[#7;+:10].[C:11]-[C:12]-[NH2;D1;+0:13]>>[#7;+:10]-[c:9]1:[c:7](-[Cl;D1;H0:8]):[#7;a:6]:[c:4](-[C;D1;H3:5]):[c:2](-[C;D1;H3:3]):[c;H0;D3;+0:1]:1-[NH;D2;+0:13]-[C:12]-[C:11] | 77.2 | [{"value": 77.2, "product": "ClC1=NC(=C(C(=C1[N+](=O)[O-])NCCCNC(OC(C)(C)C)=O)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | HOUR | A solution of tert-butyl 3-aminopropylcarbamate (121.39 g, 697 mmol) in N,N-dimethylformamide (200 mL) was slowly added to a solution of 2,4-dichloro-5,6-dimethyl-3-nitropyridine (110 g, 498 mmol) and triethylamine (104 mL, 746 mmol) in N,N-dimethylformamide (900 mL). After stirring at ambient temperature for 20 hours ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1 | HCl | CN(C=O)C | null | 20 | CC(C)(C)OC(=O)NCCCN.Cc1nc(Cl)c([N+](=O)[O-])c(Cl)c1C>CN(C=O)C>Cc1nc(Cl)c([N+](=O)[O-])c(NCCCNC(=O)OC(C)(C)C)c1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9dcc8ea355f149f1816e7eb5dc1f65b3 | CC(=O)NCCCn1c(C)nc2c(N)nc(C)c(C)c21>>Cc1nc(N)c2nc(C)n(CCCN)c2c1C | Cl.NC1=NC(=C(C2=C1N=C(N2CCCNC(C)=O)C)C)C.Cl>>NCCCN1C(=NC=2C(=NC(=C(C21)C)C)N)C | CC(=O)[NH:14][CH2:13][CH2:12][CH2:11][n:10]1[c:8]([CH3:9])[n:7][c:6]2[c:4]([NH2:5])[n:3][c:2]([CH3:1])[c:16]([CH3:17])[c:15]21>>[CH3:1][c:2]1[n:3][c:4]([NH2:5])[c:6]2[n:7][c:8]([CH3:9])[n:10]([CH2:11][CH2:12][CH2:13][NH2:14])[c:15]2[c:16]1[CH3:17] | CC(=O)NCCCn1c(C)nc2c(N)nc(C)c(C)c21 | Cc1nc(N)c2nc(C)n(CCCN)c2c1C | null | null | C(C)O | Reduction | Hydrogenolysis of amides/imides/carbamates | 755df58c254dea764fdda078ffd678ec540bba057c83683be04c253f1270ac7b | 025f7cefe51e71668ad5d09fca32df168e9b538347403e4d5c1748073e538adc | c1cc2[nH]cnc2cn1 | C-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | 62.3 | [{"value": 62.3, "product": "NCCCN1C(=NC=2C(=NC(=C(C21)C)C)N)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | DAY | Concentrated hydrochloric acid (5 mL) was slowly added to a solution of N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]acetamide (15.94 g, 57.9 mmol) in absolute ethanol (100 mL). A precipitate formed immediately and the mixture thickened. Ethanol (50 mL) was added followed by the addition of concen... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Primary amine | null | null | c1cc2nc[nH]c2cn1 | HO- | C(C)O | null | 48 | CC(=O)NCCCn1c(C)nc2c(N)nc(C)c(C)c21>C(C)O>Cc1nc(N)c2nc(C)n(CCCN)c2c1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-85bdc7c5cbc84db4b8cdfd38aca472ab | CC(C)C(=O)Cl.Cc1nc(N)c2nc(C)n(CCCN)c2c1C>>Cc1nc(N)c2nc(C)n(CCCNC(=O)C(C)C)c2c1C | C(C)N(CC)CC.NCCCN1C(=NC=2C(=NC(=C(C21)C)C)N)C.C(C(C)C)(=O)Cl>>NC1=NC(=C(C2=C1N=C(N2CCCNC(C(C)C)=O)C)C)C | Cl[C:15](=[O:16])[CH:17]([CH3:18])[CH3:19].[CH3:1][c:2]1[n:3][c:4]([NH2:5])[c:6]2[n:7][c:8]([CH3:9])[n:10]([CH2:11][CH2:12][CH2:13][NH2:14])[c:20]2[c:21]1[CH3:22]>>[CH3:1][c:2]1[n:3][c:4]([NH2:5])[c:6]2[n:7][c:8]([CH3:9])[n:10]([CH2:11][CH2:12][CH2:13][NH:14][C:15](=[O:16])[CH:17]([CH3:18])[CH3:19])[c:20]2[c:21]1[CH3:2... | CC(C)C(=O)Cl.Cc1nc(N)c2nc(C)n(CCCN)c2c1C | Cc1nc(N)c2nc(C)n(CCCNC(=O)C(C)C)c2c1C | null | null | C(Cl)(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1cc2[nH]cnc2cn1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[C;D1;H3:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[C;D1;H3:5] | 25.3 | [{"value": 25.3, "product": "NC1=NC(=C(C2=C1N=C(N2CCCNC(C(C)C)=O)C)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | Triethylamine (0.78 mL, 5.6 mmol) was added to a solution of 1-(3-aminopropyl)-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-4-amine (1.00 g, 4.3 mmol) in chloroform (50 mL). The solution was cooled in an ice bath and then isobutyryl chloride (0.49 mL, 4.7 mmol) was added. The reaction mixture was stirred for 15 minutes the... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1cc2nc[nH]c2cn1 | HCl | C(Cl)(Cl)Cl | null | 0.25 | CC(C)C(=O)Cl.Cc1nc(N)c2nc(C)n(CCCN)c2c1C>C(Cl)(Cl)Cl>Cc1nc(N)c2nc(C)n(CCCNC(=O)C(C)C)c2c1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-19266594c35b49e7a3d5c3b07fdcec2f | CCOCC(=O)Cl.Cc1nc(Oc2ccccc2)c(N)c(NCCCNC(=O)OC(C)(C)C)c1C>>CCOCc1nc2c(Oc3ccccc3)nc(C)c(C)c2n1CCCNC(=O)OC(C)(C)C | N1=CC=CC=C1.NC=1C(=NC(=C(C1NCCCNC(OC(C)(C)C)=O)C)C)OC1=CC=CC=C1.C(C)OCC(=O)Cl.[OH-].[Na+]>>C(C)OCC=1N(C2=C(C(=NC(=C2C)C)OC2=CC=CC=C2)N1)CCCNC(OC(C)(C)C)=O | O=[C:5](Cl)[CH2:4][O:3][CH2:2][CH3:1].[NH2:6][c:7]1[c:8]([O:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[n:16][c:17]([CH3:18])[c:19]([CH3:20])[c:21]1[NH:22][CH2:23][CH2:24][CH2:25][NH:26][C:27](=[O:28])[O:29][C:30]([CH3:31])([CH3:32])[CH3:33]>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([O:9][c:10]3[cH:11][cH:12... | CCOCC(=O)Cl.Cc1nc(Oc2ccccc2)c(N)c(NCCCNC(=O)OC(C)(C)C)c1C | CCOCc1nc2c(Oc3ccccc3)nc(C)c(C)c2n1CCCNC(=O)OC(C)(C)C | null | null | ClCCl.O | Aromatic Heterocycle Formation | OtherReaction | 78eafe1b5045f3b00aef70bb1a619e903ea930e21277b29c87a52bd826b163f2 | 56ef83dfadec35a1cf1db968b807e178cc4924ce15bf36d774883783cef0f450 | c1ccc(Oc2nccc3[nH]cnc23)cc1 | Cl-[C;H0;D3;+0:1](=O)-[C:2]-[#8:3].[#8:4]-[c:5]1:[#7;a:6]:[c:7]:[c:8]:[c:9](-[NH;D2;+0:10]-[C:11]-[C:12]):[c:13]:1-[NH2;D1;+0:14]>>[#8:3]-[C:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:14]:[c:13]2:[c:9](:[c:8]:[c:7]:[#7;a:6]:[c:5]:2-[#8:4]):[n;H0;D3;+0:10]:1-[C:11]-[C:12] | null | [] | null | null | 30 | MINUTE | Part A Using the general method of Example 17 Part D, a pyridine solution of tert-butyl 3-[(3-amino-5,6-dimethyl-2-phenoxypyridin-4-yl)amino]propylcarbamate (see Example 17 Part C) was treated with ethoxyacetyl chloride (21.81 g, 178 mmol). The crude product was combined with dichloromethane (2 L) and water (2 L). The ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine.Secondary amine | null | c1ccncc1 | c1cc2nc[nH]c2cn1 | c1ccccc1.c1cc2nc[nH]c2cn1 | HCl | ClCCl.O | null | 0.5 | CCOCC(=O)Cl.Cc1nc(Oc2ccccc2)c(N)c(NCCCNC(=O)OC(C)(C)C)c1C>ClCCl.O>CCOCc1nc2c(Oc3ccccc3)nc(C)c(C)c2n1CCCNC(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bb8d62be3b474153a939fe55c76cbba5 | CC(=O)[O-].CCOCc1nc2c(Oc3ccccc3)nc(C)c(C)c2n1CCCNC(=O)OC(C)(C)C.[NH4+]>>CCOCc1nc2c(N)nc(C)c(C)c2n1CCCNC(C)=O | [OH-].[Na+].C(C)(=O)OC.C(C)(=O)[O-].[NH4+].C(C)OCC=1N(C2=C(C(=NC(=C2C)C)OC2=CC=CC=C2)N1)CCCNC(OC(C)(C)C)=O.[OH-].[NH4+]>>NC1=NC(=C(C2=C1N=C(N2CCCNC(C)=O)COCC)C)C | [O-][C:21]([CH3:22])=[O:23].CC(C)(C)OC(=O)[NH:20][CH2:19][CH2:18][CH2:17][n:16]1[c:5]([CH2:4][O:3][CH2:2][CH3:1])[n:6][c:7]2[c:8](Oc3ccccc3)[n:10][c:11]([CH3:12])[c:13]([CH3:14])[c:15]21.[NH4+:9]>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]([CH3:12])[c:13]([CH3:14])[c:15]2[n:16]1[CH2:17][CH2:1... | CC(=O)[O-].CCOCc1nc2c(Oc3ccccc3)nc(C)c(C)c2n1CCCNC(=O)OC(C)(C)C.[NH4+] | CCOCc1nc2c(N)nc(C)c(C)c2n1CCCNC(C)=O | null | null | C(Cl)(Cl)Cl | Acylation | OtherReaction | 48ede7b00199b12377e56433f5549a6aeb80f3a4de3d88fa0faf9c20b60c21bf | da050e367dc508cff030bfc747da160eb0c58cd8471f5f04fe70ac7830bc23a2 | c1cc2[nH]cnc2cn1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]-[C:4]-[#7;a:5]1:[c:6]:[#7;a:7]:[c:8]2:[c:9]:1:[c:10]:[c:11]:[#7;a:12]:[c;H0;D3;+0:13]:2-O-c1:c:c:c:c:c:1.[C;D1;H3:14]-[C;H0;D3;+0:15](-[O-])=[O;D1;H0:16].[NH4+;D0:17]>>[C;D1;H3:14]-[C;H0;D3;+0:15](=[O;D1;H0:16])-[NH;D2;+0:1]-[C:2]-[C:3]-[C:4]-[#7;a:5]1:[c:6]:[#7;a:7]:[c:8]2:... | null | [] | 150 | CELSIUS | 27 | HOUR | Ammonium acetate (500 g) and tert-butyl 3-[2-(ethoxymethyl)-6,7-dimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl]propylcarbamate (35.09 g, 77 mmol) were combined in a 2 L flask. The neck of the flask was stuffed with a wad of paper towels. The reaction mixture was heated with stirring at 150° C. for 27 hours. The react... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Ether.Boc | Secondary amide.Primary amine | c1ccccc1.c1cc2[nH]cnc2cn1 | c1cc2nc[nH]c2cn1 | c1cc2nc[nH]c2cn1 | HO- | C(Cl)(Cl)Cl | 150 | 27 | CC(=O)[O-].CCOCc1nc2c(Oc3ccccc3)nc(C)c(C)c2n1CCCNC(=O)OC(C)(C)C.[NH4+]>C(Cl)(Cl)Cl>CCOCc1nc2c(N)nc(C)c(C)c2n1CCCNC(C)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cdbf41f59d6d4d6e829fa4e5b4ee6fc3 | CC(C)C(=O)Cl.CCOCc1nc2c(N)nc(C)c(C)c2n1CCCN>>CCOCc1nc2c(N)nc(C)c(C)c2n1CCCNC(=O)C(C)C | NCCCN1C(=NC=2C(=NC(=C(C21)C)C)N)COCC.C(C(C)C)(=O)Cl>>NC1=NC(=C(C2=C1N=C(N2CCCNC(C(C)C)=O)COCC)C)C | Cl[C:21](=[O:22])[CH:23]([CH3:24])[CH3:25].[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]([CH3:12])[c:13]([CH3:14])[c:15]2[n:16]1[CH2:17][CH2:18][CH2:19][NH2:20]>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]([CH3:12])[c:13]([CH3:14])[c:15]2[n:16]1[CH2:17][CH2:18][CH2:19][... | CC(C)C(=O)Cl.CCOCc1nc2c(N)nc(C)c(C)c2n1CCCN | CCOCc1nc2c(N)nc(C)c(C)c2n1CCCNC(=O)C(C)C | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1cc2[nH]cnc2cn1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[C;D1;H3:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[C;D1;H3:5] | 59.2 | [{"value": 59.2, "product": "NC1=NC(=C(C2=C1N=C(N2CCCNC(C(C)C)=O)COCC)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using the method of Example 19, 1-(3-aminopropyl)-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine (1.00 g, 3.6 mmol) was reacted with isobutyryl chloride (0.42 mL, 40 mmol) to provide 0.74 g of N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}-2-methylpropanamide as an off... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1cc2nc[nH]c2cn1 | HCl | null | null | null | CC(C)C(=O)Cl.CCOCc1nc2c(N)nc(C)c(C)c2n1CCCN>>CCOCc1nc2c(N)nc(C)c(C)c2n1CCCNC(=O)C(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-93bc3839ace74cb5bd8303c2526063ba | CC(C)(C)OC(=O)NCCN.Cc1nc(Cl)c([N+](=O)[O-])c(Cl)c1C>>Cc1nc(Cl)c([N+](=O)[O-])c(NCCNC(=O)OC(C)(C)C)c1C | ClC1=NC(=C(C(=C1[N+](=O)[O-])Cl)C)C.C(C)N(CC)CC.NCCNC(OC(C)(C)C)=O>>ClC1=NC(=C(C(=C1[N+](=O)[O-])NCCNC(OC(C)(C)C)=O)C)C | [NH2:11][CH2:12][CH2:13][NH:14][C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21].Cl[c:10]1[c:6]([N+:7](=[O:8])[O-:9])[c:4]([Cl:5])[n:3][c:2]([CH3:1])[c:22]1[CH3:23]>>[CH3:1][c:2]1[n:3][c:4]([Cl:5])[c:6]([N+:7](=[O:8])[O-:9])[c:10]([NH:11][CH2:12][CH2:13][NH:14][C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:2... | CC(C)(C)OC(=O)NCCN.Cc1nc(Cl)c([N+](=O)[O-])c(Cl)c1C | Cc1nc(Cl)c([N+](=O)[O-])c(NCCNC(=O)OC(C)(C)C)c1C | null | null | C(C)(=O)OCC.CN(C=O)C | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccncc1 | Cl-[c;H0;D3;+0:1]1:[c:2](-[C;D1;H3:3]):[c:4](-[C;D1;H3:5]):[#7;a:6]:[c:7](-[Cl;D1;H0:8]):[c:9]:1-[#7;+:10].[C:11]-[C:12]-[NH2;D1;+0:13]>>[#7;+:10]-[c:9]1:[c:7](-[Cl;D1;H0:8]):[#7;a:6]:[c:4](-[C;D1;H3:5]):[c:2](-[C;D1;H3:3]):[c;H0;D3;+0:1]:1-[NH;D2;+0:13]-[C:12]-[C:11] | 77.4 | [{"value": 77.4, "product": "ClC1=NC(=C(C(=C1[N+](=O)[O-])NCCNC(OC(C)(C)C)=O)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | A solution of 2,4-dichloro-5,6-dimethyl-3-nitropyridine (60 g, 271 mmol) in anhydrous N,N-dimethylformamide (600 mL) was cooled to 0° C. Triethylamine (44.8 mL, 326 mmol) was added drop wise followed by tert-butyl 2-aminoethylcarbamate (52.2 g, 326 mmol). After 30 minutes the ice bath was removed and the reaction mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1 | HCl | C(C)(=O)OCC.CN(C=O)C | 60 | null | CC(C)(C)OC(=O)NCCN.Cc1nc(Cl)c([N+](=O)[O-])c(Cl)c1C>C(C)(=O)OCC.CN(C=O)C>Cc1nc(Cl)c([N+](=O)[O-])c(NCCNC(=O)OC(C)(C)C)c1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d6384d48d7884598a010228de80c34f6 | Cc1nc(Cl)c([N+](=O)[O-])c(NCCNC(=O)OC(C)(C)C)c1C.Oc1ccccc1>>Cc1nc(Oc2ccccc2)c([N+](=O)[O-])c(NCCNC(=O)OC(C)(C)C)c1C | O.C1(=CC=CC=C1)O.ClC1=NC(=C(C(=C1[N+](=O)[O-])NCCNC(OC(C)(C)C)=O)C)C.[H-].[Na+]>>CC1=NC(=C(C(=C1C)NCCNC(OC(C)(C)C)=O)[N+](=O)[O-])OC1=CC=CC=C1 | Cl[c:4]1[n:3][c:2]([CH3:1])[c:28]([CH3:29])[c:16]([NH:17][CH2:18][CH2:19][NH:20][C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[c:12]1[N+:13](=[O:14])[O-:15].[OH:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1>>[CH3:1][c:2]1[n:3][c:4]([O:5][c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[c:12]([N+:13](=[O:14])[O-:15])[c:16]... | Cc1nc(Cl)c([N+](=O)[O-])c(NCCNC(=O)OC(C)(C)C)c1C.Oc1ccccc1 | Cc1nc(Oc2ccccc2)c([N+](=O)[O-])c(NCCNC(=O)OC(C)(C)C)c1C | null | null | COCCOCCOC | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 99925b30dd2603ae575cba81b58435d015cd6b7267cf347380904f25833af5f2 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(Oc2ccccn2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10]):[#7;a:2]:[c:3] | 59.1 | [{"value": 59.1, "product": "CC1=NC(=C(C(=C1C)NCCNC(OC(C)(C)C)=O)[N+](=O)[O-])OC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 30 | MINUTE | Phenol (1.19 g, 12.6 mmol) was added in portions to a chilled (0° C.) suspension of sodium hydride (0.52 g of 60%, 13.1 mmol) in diglyme (4 mL). The reaction mixture was then stirred for 30 minutes. A warm solution of tert-butyl 2-[(2-chloro-5,6-dimethyl-3-nitropyridin-4-yl)amino]ethylcarbamate (3.0 g, 8.70 mmol) in di... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccccc1 | HCl | COCCOCCOC | 90 | 0.5 | Cc1nc(Cl)c([N+](=O)[O-])c(NCCNC(=O)OC(C)(C)C)c1C.Oc1ccccc1>COCCOCCOC>Cc1nc(Oc2ccccc2)c([N+](=O)[O-])c(NCCNC(=O)OC(C)(C)C)c1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5248245f709344cab5225a5836b8c6c7 | Cc1nc(Oc2ccccc2)c([N+](=O)[O-])c(NCCNC(=O)OC(C)(C)C)c1C>>Cc1nc(Oc2ccccc2)c(N)c(NCCNC(=O)OC(C)(C)C)c1C | CC1=NC(=C(C(=C1C)NCCNC(OC(C)(C)C)=O)[N+](=O)[O-])OC1=CC=CC=C1>>NC=1C(=NC(=C(C1NCCNC(OC(C)(C)C)=O)C)C)OC1=CC=CC=C1 | O=[N+:13]([O-])[c:12]1[c:4]([O:5][c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[n:3][c:2]([CH3:1])[c:26]([CH3:27])[c:14]1[NH:15][CH2:16][CH2:17][NH:18][C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25]>>[CH3:1][c:2]1[n:3][c:4]([O:5][c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[c:12]([NH2:13])[c:14]([NH:15][CH2:16][CH2:17][NH... | Cc1nc(Oc2ccccc2)c([N+](=O)[O-])c(NCCNC(=O)OC(C)(C)C)c1C | Cc1nc(Oc2ccccc2)c(N)c(NCCNC(=O)OC(C)(C)C)c1C | null | [Pt] | CO.C1(=CC=CC=C1)C | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(Oc2ccccn2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4](-[#8:5]):[#7;a:6]:[c:7]>>[#8:5]-[c:4](:[#7;a:6]:[c:7]):[c:2](-[NH2;D1;+0:1]):[c:3] | 96.7 | [{"value": 96.7, "product": "NC=1C(=NC(=C(C1NCCNC(OC(C)(C)C)=O)C)C)OC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Catalyst (5 g of 5% platinum on carbon) was added to a warm solution of tert-butyl 2-[(2,3-dimethyl-5-nitro-6-phenoxypyridin-4-yl)amino]ethylcarbamate (50.4 g) in a mixture of toluene (500 mL) and methanol (40 mL). The mixture was placed under hydrogen pressure (50 psi, 3.4×105 Pa). After 2 hours more catalyst (4 g) wa... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccncc1.c1ccccc1 | Other | [Pt].CO.C1(=CC=CC=C1)C | null | 8 | Cc1nc(Oc2ccccc2)c([N+](=O)[O-])c(NCCNC(=O)OC(C)(C)C)c1C>[Pt].CO.C1(=CC=CC=C1)C>Cc1nc(Oc2ccccc2)c(N)c(NCCNC(=O)OC(C)(C)C)c1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b26a23f2ad984f5d9be603e103503082 | CCOC(C)(OCC)OCC.Cc1nc(Oc2ccccc2)c(N)c(NCCNC(=O)OC(C)(C)C)c1C>>Cc1nc(Oc2ccccc2)c2nc(C)n(CCNC(=O)OC(C)(C)C)c2c1C | NC=1C(=NC(=C(C1NCCNC(OC(C)(C)C)=O)C)C)OC1=CC=CC=C1.C(C)(OCC)(OCC)OCC.Cl.N1=CC=CC=C1.C1(=CC=CC=C1)C>>CC=1N(C2=C(C(=NC(=C2C)C)OC2=CC=CC=C2)N1)CCNC(OC(C)(C)C)=O | CCO[C:14](OCC)(OCC)[CH3:15].[CH3:1][c:2]1[n:3][c:4]([O:5][c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[c:12]([NH2:13])[c:27]([NH:16][CH2:17][CH2:18][NH:19][C:20](=[O:21])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])[c:28]1[CH3:29]>>[CH3:1][c:2]1[n:3][c:4]([O:5][c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[c:12]2[n:13][c:14]([CH3:15]... | CCOC(C)(OCC)OCC.Cc1nc(Oc2ccccc2)c(N)c(NCCNC(=O)OC(C)(C)C)c1C | Cc1nc(Oc2ccccc2)c2nc(C)n(CCNC(=O)OC(C)(C)C)c2c1C | null | null | C(C)(=O)OCC | Aromatic Heterocycle Formation | OtherReaction | 6c3e01c5e3852da28f9688544b7153fd8e343da3cc230cff9f10f5721233664a | a60e703c3cf5c0d933aa031358d338c45d96ec82dec3fc2d9f5dce06b9dcc651 | c1ccc(Oc2nccc3[nH]cnc23)cc1 | C-C-O-[C;H0;D4;+0:1](-[C;D1;H3:2])(-O-C-C)-O-C-C.[#8:3]-[c:4]1:[#7;a:5]:[c:6]:[c:7]:[c:8](-[NH;D2;+0:9]-[C:10]-[C:11]):[c:12]:1-[NH2;D1;+0:13]>>[#8:3]-[c:4]1:[#7;a:5]:[c:6]:[c:7]:[c:8]2:[c:12]:1:[n;H0;D2;+0:13]:[c;H0;D3;+0:1](-[C;D1;H3:2]):[n;H0;D3;+0:9]:2-[C:10]-[C:11] | 100 | [{"value": 100.0, "product": "CC=1N(C2=C(C(=NC(=C2C)C)OC2=CC=CC=C2)N1)CCNC(OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of tert-butyl 2-[(3-amino-5,6-dimethyl-2-phenoxypyridin-4-yl)amino]ethylcarbamate (43.7 g, 117 mmol), triethyl orthoacetate (22.6 mL, 123 mmol), pyridine hydrochloride (4.4 g) and toluene (440 mL) was heated at reflux for 30 minutes. The reaction mixture was concentrated under reduced pressure to provide a br... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Primary amine.Secondary amine | null | c1ccncc1 | c1cc2nc[nH]c2cn1 | c1ccccc1.c1cc2nc[nH]c2cn1 | HO- | C(C)(=O)OCC | null | null | CCOC(C)(OCC)OCC.Cc1nc(Oc2ccccc2)c(N)c(NCCNC(=O)OC(C)(C)C)c1C>C(C)(=O)OCC>Cc1nc(Oc2ccccc2)c2nc(C)n(CCNC(=O)OC(C)(C)C)c2c1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8381eaf7159647cbafadef6b071a8849 | CC(C)C(=O)Cl.Cc1nc(N)c2nc(C)n(CCN)c2c1C>>Cc1nc(N)c2nc(C)n(CCNC(=O)C(C)C)c2c1C | C(C(C)C)(=O)Cl.Cl.NCCN1C(=NC=2C(=NC(=C(C21)C)C)N)C.NCCN1C(=NC=2C(=NC(=C(C21)C)C)N)C.C(C)N(CC)CC>>NC1=NC(=C(C2=C1N=C(N2CCNC(C(C)C)=O)C)C)C | Cl[C:14](=[O:15])[CH:16]([CH3:17])[CH3:18].[CH3:1][c:2]1[n:3][c:4]([NH2:5])[c:6]2[n:7][c:8]([CH3:9])[n:10]([CH2:11][CH2:12][NH2:13])[c:19]2[c:20]1[CH3:21]>>[CH3:1][c:2]1[n:3][c:4]([NH2:5])[c:6]2[n:7][c:8]([CH3:9])[n:10]([CH2:11][CH2:12][NH:13][C:14](=[O:15])[CH:16]([CH3:17])[CH3:18])[c:19]2[c:20]1[CH3:21] | CC(C)C(=O)Cl.Cc1nc(N)c2nc(C)n(CCN)c2c1C | Cc1nc(N)c2nc(C)n(CCNC(=O)C(C)C)c2c1C | null | null | ClCCl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1cc2[nH]cnc2cn1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[C;D1;H3:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[C;D1;H3:5] | 74.5 | [{"value": 74.5, "product": "NC1=NC(=C(C2=C1N=C(N2CCNC(C(C)C)=O)C)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | Isobutyryl chloride (1.3 mL, 12.2 mmol) was added dropwise to a mixture of 1-(2-aminoethyl)-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-4-amine hydrochloride (4.0 g of material from Example 24, 12.2 mmol), triethylamine (85 mL, 610 mmol) and dichloromethane (400 mL). After 15 minutes analysis by high performance liquid ch... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1cc2nc[nH]c2cn1 | HCl | ClCCl | null | 0.25 | CC(C)C(=O)Cl.Cc1nc(N)c2nc(C)n(CCN)c2c1C>ClCCl>Cc1nc(N)c2nc(C)n(CCNC(=O)C(C)C)c2c1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d966ca48e2fb4cd1b175e12286698793 | Cc1c(O)cc(=O)[nH]c1Cl.O=[N+]([O-])O>>Cc1c(Cl)[nH]c(=O)c([N+](=O)[O-])c1O | Cl.ClC1=C(C(=CC(N1)=O)O)C.[N+](=O)(O)[O-]>>ClC1=C(C(=C(C(N1)=O)[N+](=O)[O-])O)C | [CH3:1][c:2]1[c:3]([Cl:4])[nH:5][c:6](=[O:7])[cH:8][c:12]1[OH:13].O[N+:9](=[O:10])[O-:11]>>[CH3:1][c:2]1[c:3]([Cl:4])[nH:5][c:6](=[O:7])[c:8]([N+:9](=[O:10])[O-:11])[c:12]1[OH:13] | Cc1c(O)cc(=O)[nH]c1Cl.O=[N+]([O-])O | Cc1c(Cl)[nH]c(=O)c([N+](=O)[O-])c1O | null | null | S(O)(O)(=O)=O | Functional Group Addition | Aromatic nitration with HNO3 | 0e0e1aad00a9b9831408092ddb230961720572571dbfafe14361c1f0ed3d115d | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | O=c1cccc[nH]1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[O;D1;H0:4]=[c:5]1:[#7;a:6]:[c:7]:[c:8]:[c:9](-[O;D1;H1:10]):[cH;D2;+0:11]:1>>[O;-;D1;H0:2]-[N+;H0;D3:1](=[O;D1;H0:3])-[c;H0;D3;+0:11]1:[c:9](-[O;D1;H1:10]):[c:8]:[c:7]:[#7;a:6]:[c:5]:1=[O;D1;H0:4] | null | [] | null | null | 30 | MINUTE | 6-Chloro-4-hydroxy-5-methyl-1H-pyridin-2-one hydrochloride (64 g) was dissolved in sulfuric acid (325 mL) while cooling in an ice bath. Nitric acid was added dropwise over a period of 90 minutes. The reaction mixture was allowed to stir for an additional 30 minutes and then it was poured into ice water (2 L). The resul... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1cccnc1 | c1ccncc1 | c1ccncc1 | HO- | S(O)(O)(=O)=O | null | 0.5 | Cc1c(O)cc(=O)[nH]c1Cl.O=[N+]([O-])O>S(O)(O)(=O)=O>Cc1c(Cl)[nH]c(=O)c([N+](=O)[O-])c1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-89a7d73081dd4ec88ad2f9bb812ea5b5 | CCCC(OC)(OC)OC.Cc1nc(Oc2ccccc2)c(N)c(NCCCCNC(=O)OC(C)(C)C)c1C>>CCCc1nc2c(Oc3ccccc3)nc(C)c(C)c2n1CCCCNC(=O)OC(C)(C)C | NC=1C(=NC(=C(C1NCCCCNC(OC(C)(C)C)=O)C)C)OC1=CC=CC=C1.C(CCC)(OC)(OC)OC>>CC1=C(C2=C(C(=N1)OC1=CC=CC=C1)N=C(N2CCCCNC(OC(C)(C)C)=O)CCC)C | CO[C:4](OC)(OC)[CH2:3][CH2:2][CH3:1].[NH2:5][c:6]1[c:7]([O:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[n:15][c:16]([CH3:17])[c:18]([CH3:19])[c:20]1[NH:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:26][C:27](=[O:28])[O:29][C:30]([CH3:31])([CH3:32])[CH3:33]>>[CH3:1][CH2:2][CH2:3][c:4]1[n:5][c:6]2[c:7]([O:8][c:9]3[cH:10][cH:11... | CCCC(OC)(OC)OC.Cc1nc(Oc2ccccc2)c(N)c(NCCCCNC(=O)OC(C)(C)C)c1C | CCCc1nc2c(Oc3ccccc3)nc(C)c(C)c2n1CCCCNC(=O)OC(C)(C)C | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 6c3e01c5e3852da28f9688544b7153fd8e343da3cc230cff9f10f5721233664a | a60e703c3cf5c0d933aa031358d338c45d96ec82dec3fc2d9f5dce06b9dcc651 | c1ccc(Oc2nccc3[nH]cnc23)cc1 | C-O-[C;H0;D4;+0:1](-O-C)(-O-C)-[C:2]-[C:3].[#8:4]-[c:5]1:[#7;a:6]:[c:7]:[c:8]:[c:9](-[NH;D2;+0:10]-[C:11]-[C:12]):[c:13]:1-[NH2;D1;+0:14]>>[#8:4]-[c:5]1:[#7;a:6]:[c:7]:[c:8]:[c:9]2:[c:13]:1:[n;H0;D2;+0:14]:[c;H0;D3;+0:1](-[C:2]-[C:3]):[n;H0;D3;+0:10]:2-[C:11]-[C:12] | 83.1 | [{"value": 83.1, "product": "CC1=C(C2=C(C(=N1)OC1=CC=CC=C1)N=C(N2CCCCNC(OC(C)(C)C)=O)CCC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Part A Using the general method of Example 12 Part E, tert-butyl 4-[(3-amino-5,6-dimethyl-2-phenoxypyridin-4-yl)amino]butylcarbamate (3.41 g, 8.51 mmol) was reacted with trimethyl orthobutyrate (1.50 mL, 9.37 mmol) to provide 3.2 g of crude tert-butyl 4-(6,7-dimethyl-4-phenoxy-2-propyl-1H-imidazo[4,5-c]pyridin-1-yl)but... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Primary amine.Secondary amine | null | c1ccncc1 | c1cc2nc[nH]c2cn1 | c1ccccc1.c1cc2nc[nH]c2cn1 | HO- | null | null | null | CCCC(OC)(OC)OC.Cc1nc(Oc2ccccc2)c(N)c(NCCCCNC(=O)OC(C)(C)C)c1C>>CCCc1nc2c(Oc3ccccc3)nc(C)c(C)c2n1CCCCNC(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cc77f4f09e094c4b9162f96456afaacd | CCOCc1nc2c(N)nc(C)c(C)c2n1CCC1CCNCC1.O=C(Cl)[C@@H]1C[C@H]1c1ccccc1>>CCOCc1nc2c(N)nc(C)c(C)c2n1CCC1CCN(C(=O)[C@@H]2C[C@H]2c2ccccc2)CC1 | C1(=CC=CC=C1)[C@H]1[C@@H](C1)C(=O)Cl.C(C)OCC=1N(C2=C(C(=NC(=C2C)C)N)N1)CCC1CCNCC1>>C(C)OCC=1N(C2=C(C(=NC(=C2C)C)N)N1)CCC1CCN(CC1)C(=O)[C@H]1[C@@H](C1)C1=CC=CC=C1 | [CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]([CH3:12])[c:13]([CH3:14])[c:15]2[n:16]1[CH2:17][CH2:18][CH:19]1[CH2:20][CH2:21][NH:22][CH2:34][CH2:35]1.Cl[C:23](=[O:24])[C@@H:25]1[CH2:26][C@H:27]1[c:28]1[cH:29][cH:30][cH:31][cH:32][cH:33]1>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])... | CCOCc1nc2c(N)nc(C)c(C)c2n1CCC1CCNCC1.O=C(Cl)[C@@H]1C[C@H]1c1ccccc1 | CCOCc1nc2c(N)nc(C)c(C)c2n1CCC1CCN(C(=O)[C@@H]2C[C@H]2c2ccccc2)CC1 | null | null | null | Acylation | N-alkylation of secondary amines with alkyl halides | aaa7c80569e6aa145ac8d7318e06893ee71aff0c965e85eca836522c948938d5 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C([C@@H]1C[C@H]1c1ccccc1)N1CCC(CCn2cnc3cnccc32)CC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]1-[C:4]-[C:5]-1.[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]1-[C:4]-[C:5]-1)-[C:9]-[C:10] | null | [] | null | null | null | null | Using the method of Examples 61–75, trans-2-phenyl-1-cyclopropanecarbonyl chloride was reacted with 2-(ethoxymethyl)-6,7-dimethyl-1-(2-piperidin-4-ylethyl)-1H-imidazo[4,5-c]pyridin-4-amine to provide the desired product. The observed accurate mass was 476.3039.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | C1CCNCC1 | C1CC[NH]CC1 | c1cc2nc[nH]c2cn1.C1CC[NH]CC1.C1CC1.c1ccccc1 | HCl | null | null | null | CCOCc1nc2c(N)nc(C)c(C)c2n1CCC1CCNCC1.O=C(Cl)[C@@H]1C[C@H]1c1ccccc1>>CCOCc1nc2c(N)nc(C)c(C)c2n1CCC1CCN(C(=O)[C@@H]2C[C@H]2c2ccccc2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d63943723ec344abb2ab368b9531d738 | Cc1nc(N)c2nc(C)n(CCCN)c2c1C.O=C(Cl)[C@@H]1C[C@H]1c1ccccc1>>Cc1nc(N)c2nc(C)n(CCCNC(=O)[C@@H]3C[C@H]3c3ccccc3)c2c1C | C1(=CC=CC=C1)[C@H]1[C@@H](C1)C(=O)Cl.NCCCN1C(=NC=2C(=NC(=C(C21)C)C)N)C>>NC1=NC(=C(C2=C1N=C(N2CCCNC(=O)[C@H]2[C@@H](C2)C2=CC=CC=C2)C)C)C | [CH3:1][c:2]1[n:3][c:4]([NH2:5])[c:6]2[n:7][c:8]([CH3:9])[n:10]([CH2:11][CH2:12][CH2:13][NH2:14])[c:26]2[c:27]1[CH3:28].Cl[C:15](=[O:16])[C@@H:17]1[CH2:18][C@H:19]1[c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1>>[CH3:1][c:2]1[n:3][c:4]([NH2:5])[c:6]2[n:7][c:8]([CH3:9])[n:10]([CH2:11][CH2:12][CH2:13][NH:14][C:15](=[O:16])[... | Cc1nc(N)c2nc(C)n(CCCN)c2c1C.O=C(Cl)[C@@H]1C[C@H]1c1ccccc1 | Cc1nc(N)c2nc(C)n(CCCNC(=O)[C@@H]3C[C@H]3c3ccccc3)c2c1C | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NCCCn1cnc2cnccc21)[C@@H]1C[C@H]1c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]1-[C:4]-[C:5]-1.[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]1-[C:4]-[C:5]-1 | null | [] | null | null | null | null | Using the method of Examples 78–92, trans-2-phenyl-1-cyclopropanecarbonyl chloride was reacted with 1-(3-aminopropyl)-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-4-amine to provide the desired product. The observed accurate mass was 378.2298.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1cc2nc[nH]c2cn1.C1CC1.c1ccccc1 | HCl | null | null | null | Cc1nc(N)c2nc(C)n(CCCN)c2c1C.O=C(Cl)[C@@H]1C[C@H]1c1ccccc1>>Cc1nc(N)c2nc(C)n(CCCNC(=O)[C@@H]3C[C@H]3c3ccccc3)c2c1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e0f5eb022f4447b49f0e2c6d141b3216 | CC(C)(N)CN.Cc1nc(Cl)c([N+](=O)[O-])c(Cl)c1C>>Cc1nc(Cl)c([N+](=O)[O-])c(NC(C)(C)CN)c1C | CO.C(Cl)(Cl)Cl.ClC1=NC(=C(C(=C1[N+](=O)[O-])Cl)C)C.C(C)N(CC)CC.NCC(C)(C)N>>ClC1=NC(=C(C(=C1[N+](=O)[O-])NC(CN)(C)C)C)C | [NH2:11][C:12]([CH3:13])([CH3:14])[CH2:15][NH2:16].Cl[c:10]1[c:6]([N+:7](=[O:8])[O-:9])[c:4]([Cl:5])[n:3][c:2]([CH3:1])[c:17]1[CH3:18]>>[CH3:1][c:2]1[n:3][c:4]([Cl:5])[c:6]([N+:7](=[O:8])[O-:9])[c:10]([NH:11][C:12]([CH3:13])([CH3:14])[CH2:15][NH2:16])[c:17]1[CH3:18] | CC(C)(N)CN.Cc1nc(Cl)c([N+](=O)[O-])c(Cl)c1C | Cc1nc(Cl)c([N+](=O)[O-])c(NC(C)(C)CN)c1C | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccncc1 | Cl-[c;H0;D3;+0:1]1:[c:2](-[C;D1;H3:3]):[c:4](-[C;D1;H3:5]):[#7;a:6]:[c:7](-[Cl;D1;H0:8]):[c:9]:1-[#7;+:10].[C:11]-[C:12](-[C;D1;H3:13])(-[C;D1;H3:14])-[NH2;D1;+0:15]>>[#7;+:10]-[c:9]1:[c:7](-[Cl;D1;H0:8]):[#7;a:6]:[c:4](-[C;D1;H3:5]):[c:2](-[C;D1;H3:3]):[c;H0;D3;+0:1]:1-[NH;D2;+0:15]-[C:12](-[C:11])(-[C;D1;H3:13])-[C;D... | 57.6 | [{"value": 57.6, "product": "ClC1=NC(=C(C(=C1[N+](=O)[O-])NC(CN)(C)C)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | A stirred solution of 2,4-dichloro-5,6-dimethyl-3-nitropyridine (4.42 g, 20.0 mmol) in 50 mL of anhydrous DMF, under N2, was treated with triethylamine (5.58 mL, 40.0 mol) and 1,2-diamino-2-methylpropane (2.10 mL, 20.0 mmol). After stirring for 24 h, the reaction mixture was concentrated under reduced pressure. The res... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1 | HCl | CN(C)C=O | null | 24 | CC(C)(N)CN.Cc1nc(Cl)c([N+](=O)[O-])c(Cl)c1C>CN(C)C=O>Cc1nc(Cl)c([N+](=O)[O-])c(NC(C)(C)CN)c1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8383e71ce26c415ca12d151de4500791 | CC(=O)NC(C)(C)CNc1c(C)c(C)nc(Cl)c1[N+](=O)[O-].Oc1ccccc1>>CC(=O)NC(C)(C)CNc1c(C)c(C)nc(Oc2ccccc2)c1[N+](=O)[O-] | [H-].[Na+].ClC1=NC(=C(C(=C1[N+](=O)[O-])NCC(C)(C)NC(C)=O)C)C.CCOC(=O)C.C1(=CC=CC=C1)O>>CC1=NC(=C(C(=C1C)NCC(C)(C)NC(C)=O)[N+](=O)[O-])OC1=CC=CC=C1 | Cl[c:16]1[n:15][c:13]([CH3:14])[c:11]([CH3:12])[c:10]([NH:9][CH2:8][C:5]([NH:4][C:2]([CH3:1])=[O:3])([CH3:6])[CH3:7])[c:24]1[N+:25](=[O:26])[O-:27].[OH:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[CH3:1][C:2](=[O:3])[NH:4][C:5]([CH3:6])([CH3:7])[CH2:8][NH:9][c:10]1[c:11]([CH3:12])[c:13]([CH3:14])[n:15][c:16]([O:17]... | CC(=O)NC(C)(C)CNc1c(C)c(C)nc(Cl)c1[N+](=O)[O-].Oc1ccccc1 | CC(=O)NC(C)(C)CNc1c(C)c(C)nc(Oc2ccccc2)c1[N+](=O)[O-] | null | null | C(OC)COC | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 99925b30dd2603ae575cba81b58435d015cd6b7267cf347380904f25833af5f2 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(Oc2ccccn2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10]):[#7;a:2]:[c:3] | 72.5 | [{"value": 50.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.5, "product": "CC1=NC(=C(C(=C1C)NCC(C)(C)NC(C)=O)[N+](=O)[O-])OC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | A 250 mL-round bottom flask was charged with NaH (60% oil dispersion, 534 mg, 13.3 mmol) under N2. The NaH was washed with three portions of hexanes and dried under a stream of N2. Dimethoxyethane (10 mL) was then added to the flask followed by phenol (1.25 g, 13.3 mmol). After stirring for 10 min, a solution of N-{2-[... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccccc1 | HCl | C(OC)COC | null | 0.166667 | CC(=O)NC(C)(C)CNc1c(C)c(C)nc(Cl)c1[N+](=O)[O-].Oc1ccccc1>C(OC)COC>CC(=O)NC(C)(C)CNc1c(C)c(C)nc(Oc2ccccc2)c1[N+](=O)[O-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4b91581460584fbea73b69f94aff02bc | CC(=O)NC(C)(C)CNc1c(C)c(C)nc(Oc2ccccc2)c1[N+](=O)[O-]>>CC(=O)NC(C)(C)CNc1c(C)c(C)nc(Oc2ccccc2)c1N | CC1=NC(=C(C(=C1C)NCC(C)(C)NC(C)=O)[N+](=O)[O-])OC1=CC=CC=C1>>NC=1C(=NC(=C(C1NCC(C)(C)NC(C)=O)C)C)OC1=CC=CC=C1 | O=[N+:25]([O-])[c:24]1[c:10]([NH:9][CH2:8][C:5]([NH:4][C:2]([CH3:1])=[O:3])([CH3:6])[CH3:7])[c:11]([CH3:12])[c:13]([CH3:14])[n:15][c:16]1[O:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[CH3:1][C:2](=[O:3])[NH:4][C:5]([CH3:6])([CH3:7])[CH2:8][NH:9][c:10]1[c:11]([CH3:12])[c:13]([CH3:14])[n:15][c:16]([O:17][c:18]2[cH:1... | CC(=O)NC(C)(C)CNc1c(C)c(C)nc(Oc2ccccc2)c1[N+](=O)[O-] | CC(=O)NC(C)(C)CNc1c(C)c(C)nc(Oc2ccccc2)c1N | null | null | C1(=CC=CC=C1)C | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(Oc2ccccn2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4](-[#8:5]):[#7;a:6]:[c:7]>>[#8:5]-[c:4](:[#7;a:6]:[c:7]):[c:2](-[NH2;D1;+0:1]):[c:3] | 81.5 | [{"value": 81.5, "product": "NC=1C(=NC(=C(C1NCC(C)(C)NC(C)=O)C)C)OC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | N-{2-[(2,3-dimethyl-5-nitro-6-phenoxypyridin-4-yl)amino]-1,1-dimethylethyl}acetamide (2.40 g, 6.45 mmol) was dissolved in 20 mL of toluene and treated with 0.2 g of Pt (5% on carbon). The reaction mixture was then shaken under H2 (3 atm) for 24 h. Then reaction mixture was then treated with an additional 1.5 g of Pt (5... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccncc1.c1ccccc1 | Other | C1(=CC=CC=C1)C | null | 24 | CC(=O)NC(C)(C)CNc1c(C)c(C)nc(Oc2ccccc2)c1[N+](=O)[O-]>C1(=CC=CC=C1)C>CC(=O)NC(C)(C)CNc1c(C)c(C)nc(Oc2ccccc2)c1N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b80539dc2ef344d398c44bf5d354c5d7 | CC(=O)NC(C)(C)CNc1c(C)c(C)nc(Oc2ccccc2)c1N.CCOCC(=O)Cl>>CCOCc1nc2c(Oc3ccccc3)nc(C)c(C)c2n1CC(C)(C)NC(C)=O | NC=1C(=NC(=C(C1NCC(C)(C)NC(C)=O)C)C)OC1=CC=CC=C1.C(C)N(CC)CC.C(C)OCC(=O)Cl>>C(C)OCC=1N(C2=C(C(=NC(=C2C)C)OC2=CC=CC=C2)N1)CC(C)(C)NC(C)=O | [NH2:6][c:7]1[c:8]([O:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[n:16][c:17]([CH3:18])[c:19]([CH3:20])[c:21]1[NH:22][CH2:23][C:24]([CH3:25])([CH3:26])[NH:27][C:28]([CH3:29])=[O:30].O=[C:5](Cl)[CH2:4][O:3][CH2:2][CH3:1]>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([O:9][c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]... | CC(=O)NC(C)(C)CNc1c(C)c(C)nc(Oc2ccccc2)c1N.CCOCC(=O)Cl | CCOCc1nc2c(Oc3ccccc3)nc(C)c(C)c2n1CC(C)(C)NC(C)=O | null | null | C(Cl)Cl | Aromatic Heterocycle Formation | OtherReaction | 78eafe1b5045f3b00aef70bb1a619e903ea930e21277b29c87a52bd826b163f2 | 56ef83dfadec35a1cf1db968b807e178cc4924ce15bf36d774883783cef0f450 | c1ccc(Oc2nccc3[nH]cnc23)cc1 | Cl-[C;H0;D3;+0:1](=O)-[C:2]-[#8:3].[#8:4]-[c:5]1:[#7;a:6]:[c:7]:[c:8]:[c:9](-[NH;D2;+0:10]-[C:11]-[C:12]):[c:13]:1-[NH2;D1;+0:14]>>[#8:3]-[C:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:14]:[c:13]2:[c:9](:[c:8]:[c:7]:[#7;a:6]:[c:5]:2-[#8:4]):[n;H0;D3;+0:10]:1-[C:11]-[C:12] | 45.6 | [{"value": 45.6, "product": "C(C)OCC=1N(C2=C(C(=NC(=C2C)C)OC2=CC=CC=C2)N1)CC(C)(C)NC(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of N-{2-[(3-amino-5,6-dimethyl-2-phenoxypyridin-4-yl)amino]-1,1-dimethylethyl}acetamide (1.80 g, 5.23 mmol) in 50 mL of CH2Cl2 was cooled to 0° C., under N2, and treated with triethylamine (728 μL, 5.23 mmol) and ethoxyacetyl chloride (574 μL, 5.23 mmol). After stirring overnight, the reaction mixture was co... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine.Secondary amine | null | c1ccncc1 | c1cc2nc[nH]c2cn1 | c1ccccc1.c1cc2nc[nH]c2cn1 | HCl | C(Cl)Cl | null | 8 | CC(=O)NC(C)(C)CNc1c(C)c(C)nc(Oc2ccccc2)c1N.CCOCC(=O)Cl>C(Cl)Cl>CCOCc1nc2c(Oc3ccccc3)nc(C)c(C)c2n1CC(C)(C)NC(C)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9da5b5b2fd204d81b6f1ad22863239e7 | CCOCc1nc2c(Oc3ccccc3)nc(C)c(C)c2n1CC(C)(C)NC(C)=O.[NH4+]>>CCOCc1nc2c(N)nc(C)c(C)c2n1CC(C)(C)NC(C)=O | C(C)OCC=1N(C2=C(C(=NC(=C2C)C)OC2=CC=CC=C2)N1)CC(C)(C)NC(C)=O.C(C)(=O)[O-].[NH4+].[NH4+].[OH-]>>[NH4+].[OH-].NC1=NC(=C(C2=C1N=C(N2CC(C)(C)NC(C)=O)COCC)C)C | c1ccc(O[c:8]2[c:7]3[n:6][c:5]([CH2:4][O:3][CH2:2][CH3:1])[n:16]([CH2:17][C:18]([CH3:19])([CH3:20])[NH:21][C:22]([CH3:23])=[O:24])[c:15]3[c:13]([CH3:14])[c:11]([CH3:12])[n:10]2)cc1.[NH4+:9]>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]([CH3:12])[c:13]([CH3:14])[c:15]2[n:16]1[CH2:17][C:18]([CH3:1... | CCOCc1nc2c(Oc3ccccc3)nc(C)c(C)c2n1CC(C)(C)NC(C)=O.[NH4+] | CCOCc1nc2c(N)nc(C)c(C)c2n1CC(C)(C)NC(C)=O | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | f1a3cc602ce132f4b138aaff43e359cc4e4ed2f1a7bdd06ecc27d202417b41fd | 4764b8d6a7ad8d9253070fdb827f95d720ac9a4f642f3b03b75fe3f308c3d0a7 | c1cc2[nH]cnc2cn1 | [C:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]2:[c:6]:1:[c:7]:[c:8]:[#7;a:9]:[c;H0;D3;+0:10]:2-O-c1:c:c:c:c:c:1.[NH4+;D0:11]>>[C:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]2:[c:6]:1:[c:7]:[c:8]:[#7;a:9]:[c;H0;D3;+0:10]:2-[NH2;D1;+0:11] | 146.6 | [{"value": 146.6, "product": "NC1=NC(=C(C2=C1N=C(N2CC(C)(C)NC(C)=O)COCC)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 160 | CELSIUS | 24 | HOUR | A pressure flask was charged with N-{2-[2-(ethoxymethyl)-6,7-dimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl]-1,1-dimethylethyl}acetamide (980 mg, 2.39 mmol) and ammonium acetate (1.25 g). The flask was sealed and heated to 160° C. The solids soon melted to give a viscous oil and heating was continued for 24 h. The re... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Primary amine | c1ccccc1.c1cc2nc[nH]c2cn1 | c1cc2nc[nH]c2cn1 | c1cc2nc[nH]c2cn1 | HO- | O | 160 | 24 | CCOCc1nc2c(Oc3ccccc3)nc(C)c(C)c2n1CC(C)(C)NC(C)=O.[NH4+]>O>CCOCc1nc2c(N)nc(C)c(C)c2n1CC(C)(C)NC(C)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-38834526cadc4d40971a9b48554cd939 | CN(C)CCOC(c1ccccc1)c1ccc(C(=O)Cl)cc1.Cc1nc(N)c2ncn(CCCCN)c2c1C>>Cc1nc(N)c2ncn(CCCCNC(=O)c3ccc(C(OCCN(C)C)c4ccccc4)cc3)c2c1C | O.CN(CCOC(C1=CC=C(C(=O)Cl)C=C1)C1=CC=CC=C1)C.NC1=NC(=C(C2=C1N=CN2CCCCN)C)C.C(C)N(CC)CC>>NC1=NC(=C(C2=C1N=CN2CCCCNC(C2=CC=C(C=C2)C(C2=CC=CC=C2)OCCN(C)C)=O)C)C | Cl[C:15](=[O:16])[c:17]1[cH:18][cH:19][c:20]([CH:21]([O:22][CH2:23][CH2:24][N:25]([CH3:26])[CH3:27])[c:28]2[cH:29][cH:30][cH:31][cH:32][cH:33]2)[cH:34][cH:35]1.[CH3:1][c:2]1[n:3][c:4]([NH2:5])[c:6]2[n:7][cH:8][n:9]([CH2:10][CH2:11][CH2:12][CH2:13][NH2:14])[c:36]2[c:37]1[CH3:38]>>[CH3:1][c:2]1[n:3][c:4]([NH2:5])[c:6]2[n... | CN(C)CCOC(c1ccccc1)c1ccc(C(=O)Cl)cc1.Cc1nc(N)c2ncn(CCCCN)c2c1C | Cc1nc(N)c2ncn(CCCCNC(=O)c3ccc(C(OCCN(C)C)c4ccccc4)cc3)c2c1C | null | CN(C1=CC=NC=C1)C | CN(C=O)C | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NCCCCn1cnc2cnccc21)c1ccc(Cc2ccccc2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 1 | HOUR | 4-[[2-(Dimethylamino)ethoxy](phenyl)methyl]benzoyl chloride (1 equivalent) was added dropwise to a suspension of 4-(4-amino-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butan-1-amine (0.22 g) in N,N-dimethylformamide (7 ml). At 1 hour, triethylamine (2 equivalents) was added followed by the addition at 2 hours of a small... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1cc2nc[nH]c2cn1.c1ccccc1.c1ccccc1 | HCl | CN(C1=CC=NC=C1)C.CN(C=O)C | null | 1 | CN(C)CCOC(c1ccccc1)c1ccc(C(=O)Cl)cc1.Cc1nc(N)c2ncn(CCCCN)c2c1C>CN(C1=CC=NC=C1)C.CN(C=O)C>Cc1nc(N)c2ncn(CCCCNC(=O)c3ccc(C(OCCN(C)C)c4ccccc4)cc3)c2c1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5c81a3b3502a410b88b65a8da4ebe4d9 | CCOC(=O)C(OCC)[P+](c1ccccc1)(c1ccccc1)c1ccccc1.O=Cc1cccc2[nH]ccc12>>CCOC(=O)/C(=C/c1cccc2[nH]ccc12)OCC | [Cl-].C(C)OC(C(=O)OCC)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.CN(C(N(C)C)=N)C.CN(C(N(C)C)=N)C.C(=O)C1=C2C=CNC2=CC=C1>>C(C)OC(/C(=C/C1=C2C=CNC2=CC=C1)/OCC)=O | c1ccc([P+](c2ccccc2)(c2ccccc2)[CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[O:17][CH2:18][CH3:19])cc1.O=[CH:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[nH:13][cH:14][cH:15][c:16]12>>[CH3:1][CH2:2][O:3][C:4](=[O:5])/[C:6](=[CH:7]/[c:8]1[cH:9][cH:10][cH:11][c:12]2[nH:13][cH:14][cH:15][c:16]12)[O:17][CH2:18][CH3:19] | CCOC(=O)C(OCC)[P+](c1ccccc1)(c1ccccc1)c1ccccc1.O=Cc1cccc2[nH]ccc12 | CCOC(=O)/C(=C/c1cccc2[nH]ccc12)OCC | null | null | ClCCl | C-C Coupling | OtherReaction | a8294defd4b8d74de5e142540264f989d52abe34ed349755f1e2199953ac5d1f | ad62a0adadbf9069bf98289a96ce8b021437ecd0412624495fbcba2ade6d16f3 | c1ccc2[nH]ccc2c1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4]:[c:5]:[#7;a:6].[C:7]-[#8:8]-[CH;D3;+0:9](-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13])-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[#7;a:6]:[c:5]:[c:4]:[c:2](/[CH;D2;+0:1]=[C;H0;D3;+0:9](\[#8:8]-[C:7])-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13]):[c:3] | 107.2 | [{"value": 107.2, "product": "C(C)OC(/C(=C/C1=C2C=CNC2=CC=C1)/OCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a solution of 35.01 g (81.6 mmol) of (1,2-diethoxy-2-oxoethyl)triphenyl phosphonium chloride in 200 ml of dichloromethane was added at 0° C. 11.01 ml (87.1 mmol) of tetramethyl guanidine and the mixture was warmed to 22° C. The mixture was treated with 7.9 g (54.4 mmol) of 4-formyl-indole and stirring was continued ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester.Ether | Ester.Ether | c1ccccc1.c1ccccc1.c1ccccc1 | null | c1ccc2[nH]ccc2c1 | HO- | ClCCl | null | 16 | CCOC(=O)C(OCC)[P+](c1ccccc1)(c1ccccc1)c1ccccc1.O=Cc1cccc2[nH]ccc12>ClCCl>CCOC(=O)/C(=C/c1cccc2[nH]ccc12)OCC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-721817e573834a32927246bb40fe9b53 | CCOC(=O)/C(=C/c1cccc2[nH]ccc12)OCC>>CCOC(=O)C(Cc1cccc2[nH]ccc12)OCC | C(C)OC(/C(=C/C1=C2C=CNC2=CC=C1)/OCC)=O.[H][H]>>C(C)OC(C(CC1=C2C=CNC2=CC=C1)OCC)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])/[C:6](=[CH:7]/[c:8]1[cH:9][cH:10][cH:11][c:12]2[nH:13][cH:14][cH:15][c:16]12)[O:17][CH2:18][CH3:19]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[nH:13][cH:14][cH:15][c:16]12)[O:17][CH2:18][CH3:19] | CCOC(=O)/C(=C/c1cccc2[nH]ccc12)OCC | CCOC(=O)C(Cc1cccc2[nH]ccc12)OCC | null | [Pd] | CCO | Reduction | Hydrogenation (double to single) | d0e0332973c77aabb8c3717dddd351d2250737d1acb0f694289dece8c206d06e | fc479563bf5f932f09579579b5e31753bf159d03a224d56dc67a29b9e37b0ad6 | c1ccc2[nH]ccc2c1 | [#7;a:1]:[c:2]:[c:3]:[c:4](/[CH;D2;+0:5]=[C;H0;D3;+0:6](\[#8:7]-[C:8])-[C:9](=[O;D1;H0:10])-[#8:11]-[C:12]):[c:13]>>[#7;a:1]:[c:2]:[c:3]:[c:4](-[CH2;D2;+0:5]-[CH;D3;+0:6](-[#8:7]-[C:8])-[C:9](=[O;D1;H0:10])-[#8:11]-[C:12]):[c:13] | 81.2 | [{"value": 81.2, "product": "C(C)OC(C(CC1=C2C=CNC2=CC=C1)OCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A suspension of 15.0 g of (Z)-2-ethoxy-3-(1H-indol-4-yl)-acrylic acid ethyl ester in 250 ml of EtOH and 3.08 g of Pd/C (10%) was hydrogenated at 22° C. for 2 h, after which time hydrogen uptake ceased. The suspension was filtered, the filtrate evaporated and the residue chromatographed on silica gel (eluent: gradient o... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether | Ester.Ether | null | null | c1ccc2[nH]ccc2c1 | null | [Pd].CCO | null | 2 | CCOC(=O)/C(=C/c1cccc2[nH]ccc12)OCC>[Pd].CCO>CCOC(=O)C(Cc1cccc2[nH]ccc12)OCC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2bbd1173503f43e4a80adb2b4bc005c0 | CCOC(=O)C(Cc1cccc2[nH]ccc12)OCC.COc1cc(OC)cc(-c2nc(CCl)c(C)o2)c1>>CCOC(=O)C(Cc1cccc2c1ccn2Cc1nc(-c2cc(OC)cc(OC)c2)oc1C)OCC | [H-].[Na+].C(C)OC(C(CC1=C2C=CNC2=CC=C1)OCC)=O.ClCC=1N=C(OC1C)C1=CC(=CC(=C1)OC)OC>>C(C)OC(C(CC1=C2C=CN(C2=CC=C1)CC=1N=C(OC1C)C1=CC(=CC(=C1)OC)OC)OCC)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[c:13]1[cH:14][cH:15][nH:16]2)[O:34][CH2:35][CH3:36].Cl[CH2:17][c:18]1[n:19][c:20](-[c:21]2[cH:22][c:23]([O:24][CH3:25])[cH:26][c:27]([O:28][CH3:29])[cH:30]2)[o:31][c:32]1[CH3:33]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][c:8]1[cH:9][c... | CCOC(=O)C(Cc1cccc2[nH]ccc12)OCC.COc1cc(OC)cc(-c2nc(CCl)c(C)o2)c1 | CCOC(=O)C(Cc1cccc2c1ccn2Cc1nc(-c2cc(OC)cc(OC)c2)oc1C)OCC | null | null | O.CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 558bcff26233c13696ebcbebe920e2039c7ee6d2503304edb672d21289ef564c | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(-c2nc(Cn3ccc4ccccc43)co2)cc1 | Cl-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#8;a:5]:[c:6]:1-[C;D1;H3:7].[c:8]:[c:9]1:[c:10]:[c:11]:[c:12]:[nH;D2;+0:13]:1>>[C;D1;H3:7]-[c:6]1:[#8;a:5]:[c:4]:[#7;a:3]:[c:2]:1-[CH2;D2;+0:1]-[n;H0;D3;+0:13]1:[c:12]:[c:11]:[c:10]:[c:9]:1:[c:8] | 84 | [{"value": 84.0, "product": "C(C)OC(C(CC1=C2C=CN(C2=CC=C1)CC=1N=C(OC1C)C1=CC(=CC(=C1)OC)OC)OCC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.8, "product": "C(C)OC(C(CC1=C2C=CN(C2=CC=C1)CC=1N=C(OC1C)C1=CC(=CC(=C1)OC)OC)OCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | 0.048 g (1.10 mmol) Sodium hydride (55% in mineral oil) was added in one portion below 5° C. and under argon to a stirred solution of 0.261 g (1.00 mmol) rac-2-ethoxy-3-(1H-indol-4-yl)-propionic acid ethyl ester and 0.321 g (1.20 mmol) 4-chloromethyl-2-(3,5-dimethoxy-phenyl)-5-methyl-oxazole in 15.0 ml N,N-dimethylform... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2[nH]ccc2c1 | c1cccc2[nH]ccc12 | c1cccc2[nH]ccc12.c1cocn1.c1ccccc1 | HCl | O.CN(C=O)C | null | 16 | CCOC(=O)C(Cc1cccc2[nH]ccc12)OCC.COc1cc(OC)cc(-c2nc(CCl)c(C)o2)c1>O.CN(C=O)C>CCOC(=O)C(Cc1cccc2c1ccn2Cc1nc(-c2cc(OC)cc(OC)c2)oc1C)OCC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0399fb9c8f3b4bd0ae21245113911683 | CCOC(=O)C(Cc1cccc2c1ccn2Cc1nc(-c2cc(OC)cc(OC)c2)oc1C)OCC>>CCOC(Cc1cccc2c1ccn2Cc1nc(-c2cc(OC)cc(OC)c2)oc1C)C(=O)O | Cl.[Li+].[OH-].C(C)OC(C(CC1=C2C=CN(C2=CC=C1)CC=1N=C(OC1C)C1=CC(=CC(=C1)OC)OC)OCC)=O>>COC=1C=C(C=C(C1)OC)C=1OC(=C(N1)CN1C=CC2=C(C=CC=C12)CC(C(=O)O)OCC)C | CC[O:34][C:32]([CH:4]([O:3][CH2:2][CH3:1])[CH2:5][c:6]1[cH:7][cH:8][cH:9][c:10]2[c:11]1[cH:12][cH:13][n:14]2[CH2:15][c:16]1[n:17][c:18](-[c:19]2[cH:20][c:21]([O:22][CH3:23])[cH:24][c:25]([O:26][CH3:27])[cH:28]2)[o:29][c:30]1[CH3:31])=[O:33]>>[CH3:1][CH2:2][O:3][CH:4]([CH2:5][c:6]1[cH:7][cH:8][cH:9][c:10]2[c:11]1[cH:12]... | CCOC(=O)C(Cc1cccc2c1ccn2Cc1nc(-c2cc(OC)cc(OC)c2)oc1C)OCC | CCOC(Cc1cccc2c1ccn2Cc1nc(-c2cc(OC)cc(OC)c2)oc1C)C(=O)O | null | null | O1CCOCC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(-c2nc(Cn3ccc4ccccc43)co2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 66 | [{"value": 66.0, "product": "COC=1C=C(C=C(C1)OC)C=1OC(=C(N1)CN1C=CC2=C(C=CC=C12)CC(C(=O)O)OCC)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.9, "product": "COC=1C=C(C=C(C1)OC)C=1OC(=C(N1)CN1C=CC2=C(C=CC=C12)CC(C(=O)O)OCC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | rac-3-{1-[2-(3,5-Dimethoxy-phenyl)-5-methyl-oxazol-4-ylmethyl]-1H-indol-4-yl}-2-ethoxy-propionic acid ethyl ester (0.390 g, 0.79 mmol ) was dissolved in 15 ml of dioxane; 1.98 ml of an aqueous solution of LiOH (1.0 molar, 1.98 mmol) were then added at room temperature. The resulting mixture was stirred overnight at roo... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cccc2[nH]ccc12.c1cocn1.c1ccccc1 | Other | O1CCOCC1 | null | 8 | CCOC(=O)C(Cc1cccc2c1ccn2Cc1nc(-c2cc(OC)cc(OC)c2)oc1C)OCC>O1CCOCC1>CCOC(Cc1cccc2c1ccn2Cc1nc(-c2cc(OC)cc(OC)c2)oc1C)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-31c59377d3ed4ee5b59f2350b8a42011 | CCOC(=O)C(Cc1cccc2[nH]ccc12)OCC.Cc1oc(-c2ccc(C(C)C)cc2)nc1CCl>>CCOC(=O)C(Cc1cccc2c1ccn2Cc1nc(-c2ccc(C(C)C)cc2)oc1C)OCC | C(C)OC(C(CC1=C2C=CNC2=CC=C1)OCC)=O.ClCC=1N=C(OC1C)C1=CC=C(C=C1)C(C)C.[H-].[Na+]>>C(C)OC(C(CC1=C2C=CN(C2=CC=C1)CC=1N=C(OC1C)C1=CC=C(C=C1)C(C)C)OCC)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[c:13]1[cH:14][cH:15][nH:16]2)[O:33][CH2:34][CH3:35].Cl[CH2:17][c:18]1[n:19][c:20](-[c:21]2[cH:22][cH:23][c:24]([CH:25]([CH3:26])[CH3:27])[cH:28][cH:29]2)[o:30][c:31]1[CH3:32]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][c:8]1[cH:9][cH:10... | CCOC(=O)C(Cc1cccc2[nH]ccc12)OCC.Cc1oc(-c2ccc(C(C)C)cc2)nc1CCl | CCOC(=O)C(Cc1cccc2c1ccn2Cc1nc(-c2ccc(C(C)C)cc2)oc1C)OCC | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 558bcff26233c13696ebcbebe920e2039c7ee6d2503304edb672d21289ef564c | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(-c2nc(Cn3ccc4ccccc43)co2)cc1 | Cl-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#8;a:5]:[c:6]:1-[C;D1;H3:7].[c:8]:[c:9]1:[c:10]:[c:11]:[c:12]:[nH;D2;+0:13]:1>>[C;D1;H3:7]-[c:6]1:[#8;a:5]:[c:4]:[#7;a:3]:[c:2]:1-[CH2;D2;+0:1]-[n;H0;D3;+0:13]1:[c:12]:[c:11]:[c:10]:[c:9]:1:[c:8] | null | [] | null | null | null | null | In analogy to the procedures described in examples 1 a] and 1 b], rac-2-ethoxy-3-(1H-indol-4-yl)-propionic acid ethyl ester was reacted with 4-chloromethyl-2-(4-isopropyl-phenyl)-5-methyl-oxazole in N,N-dimethylformamide in the presence of sodium hydride to yield rac-3-{1-[2-(4-isopropyl-phenyl)-5-methyl-oxazol-4-ylmet... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2[nH]ccc2c1 | c1cccc2[nH]ccc12 | c1cccc2[nH]ccc12.c1cocn1.c1ccccc1 | HCl | CN(C=O)C | null | null | CCOC(=O)C(Cc1cccc2[nH]ccc12)OCC.Cc1oc(-c2ccc(C(C)C)cc2)nc1CCl>CN(C=O)C>CCOC(=O)C(Cc1cccc2c1ccn2Cc1nc(-c2ccc(C(C)C)cc2)oc1C)OCC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a481b5cc2a034aed9fac6e601a0a3d36 | CCOC(=O)C(Cc1cccc2[nH]ccc12)OCC.Cc1oc(-c2ccccc2)nc1CCCOS(C)(=O)=O>>CCOC(=O)C(Cc1cccc2c1ccn2CCCc1nc(-c2ccccc2)oc1C)OCC | C(C)OC(C(CC1=C2C=CNC2=CC=C1)OCC)=O.CC1=C(N=C(O1)C1=CC=CC=C1)CCCOS(=O)(=O)C.[H-].[Na+]>>C(C)OC(C(CC1=C2C=CN(C2=CC=C1)CCCC=1N=C(OC1C)C1=CC=CC=C1)OCC)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[c:13]1[cH:14][cH:15][nH:16]2)[O:32][CH2:33][CH3:34].CS(=O)(=O)O[CH2:17][CH2:18][CH2:19][c:20]1[n:21][c:22](-[c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[o:29][c:30]1[CH3:31]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][c:8]1[cH:9][cH:10]... | CCOC(=O)C(Cc1cccc2[nH]ccc12)OCC.Cc1oc(-c2ccccc2)nc1CCCOS(C)(=O)=O | CCOC(=O)C(Cc1cccc2c1ccn2CCCc1nc(-c2ccccc2)oc1C)OCC | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | a5a4d808717e5464e10e995bbfbb6f0216f658363978ee91898622a4996bf96c | 0b4f3c8c88df0a792d0db7d59004d7fe5681a61dd48ef2449ddca2d636f76ada | c1ccc(-c2nc(CCCn3ccc4ccccc43)co2)cc1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]-[C:3].[c:4]:[c:5]1:[c:6]:[c:7]:[c:8]:[nH;D2;+0:9]:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:9]1:[c:8]:[c:7]:[c:6]:[c:5]:1:[c:4] | null | [] | null | null | null | null | In analogy to the procedures described in examples 1 a] and 1 b], rac-2-ethoxy-3-(1H-indol-4-yl)-propionic acid ethyl ester was reacted with methanesulfonic acid 3-(5-methyl-2-phenyl-oxazol-4-yl)-propyl ester in N,N-dimethylformamide in the presence of sodium hydride to yield rac-2-ethoxy-3-{1-[3-(5-methyl-2-phenyl-oxa... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate | null | c1ccc2[nH]ccc2c1 | c1cccc2[nH]ccc12 | c1cccc2[nH]ccc12.c1cocn1.c1ccccc1 | MsOH.HO- | CN(C=O)C | null | null | CCOC(=O)C(Cc1cccc2[nH]ccc12)OCC.Cc1oc(-c2ccccc2)nc1CCCOS(C)(=O)=O>CN(C=O)C>CCOC(=O)C(Cc1cccc2c1ccn2CCCc1nc(-c2ccccc2)oc1C)OCC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d08ee7657af449f690fb75fdfd1f006b | CCOC(=O)C(Cc1cccc2[nH]ccc12)OCC.Cc1oc(-c2ccccc2)nc1CCOS(C)(=O)=O>>CCOC(=O)C(Cc1cccc2c1ccn2CCc1nc(-c2ccccc2)oc1C)OCC | C(C)OC(C(CC1=C2C=CNC2=CC=C1)OCC)=O.CC1=C(N=C(O1)C1=CC=CC=C1)CCOS(=O)(=O)C.[H-].[Na+]>>C(C)OC(C(CC1=C2C=CN(C2=CC=C1)CCC=1N=C(OC1C)C1=CC=CC=C1)OCC)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[c:13]1[cH:14][cH:15][nH:16]2)[O:31][CH2:32][CH3:33].CS(=O)(=O)O[CH2:17][CH2:18][c:19]1[n:20][c:21](-[c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[o:28][c:29]1[CH3:30]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][c:8]1[cH:9][cH:10][cH:11][... | CCOC(=O)C(Cc1cccc2[nH]ccc12)OCC.Cc1oc(-c2ccccc2)nc1CCOS(C)(=O)=O | CCOC(=O)C(Cc1cccc2c1ccn2CCc1nc(-c2ccccc2)oc1C)OCC | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | a5a4d808717e5464e10e995bbfbb6f0216f658363978ee91898622a4996bf96c | 0b4f3c8c88df0a792d0db7d59004d7fe5681a61dd48ef2449ddca2d636f76ada | c1ccc(-c2nc(CCn3ccc4ccccc43)co2)cc1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]-[c:3](:[#7;a:4]):[c:5]:[#8;a:6].[c:7]:[c:8]1:[c:9]:[c:10]:[c:11]:[nH;D2;+0:12]:1>>[#7;a:4]:[c:3](-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:12]1:[c:11]:[c:10]:[c:9]:[c:8]:1:[c:7]):[c:5]:[#8;a:6] | null | [] | null | null | null | null | In analogy to the procedures described in examples 1 a] and 1 b], rac-2-ethoxy-3-(1H-indol-4-yl)-propionic acid ethyl ester was reacted with methanesulfonic acid 2-(5-methyl-2-phenyl-oxazol-4-yl)-ethyl ester in N,N-dimethylformamide in the presence of sodium hydride to yield rac-2-ethoxy-3-{1-[2-(5-methyl-2-phenyl-oxaz... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate | null | c1ccc2[nH]ccc2c1 | c1cccc2[nH]ccc12 | c1cccc2[nH]ccc12.c1cocn1.c1ccccc1 | MsOH.HO- | CN(C=O)C | null | null | CCOC(=O)C(Cc1cccc2[nH]ccc12)OCC.Cc1oc(-c2ccccc2)nc1CCOS(C)(=O)=O>CN(C=O)C>CCOC(=O)C(Cc1cccc2c1ccn2CCc1nc(-c2ccccc2)oc1C)OCC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8f3f4dd495c149d096e60f2e3399d620 | CCOC(=O)C(Cc1cccc2[nH]ccc12)OCC.Cc1oc(-c2ccccc2)nc1CCl>>CCOC(=O)C(Cc1cccc2c1ccn2Cc1nc(-c2ccccc2)oc1C)OCC | C(C)OC(C(CC1=C2C=CNC2=CC=C1)OCC)=O.ClCC=1N=C(OC1C)C1=CC=CC=C1.[H-].[Na+]>>C(C)OC(C(CC1=C2C=CN(C2=CC=C1)CC=1N=C(OC1C)C1=CC=CC=C1)OCC)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[c:13]1[cH:14][cH:15][nH:16]2)[O:30][CH2:31][CH3:32].Cl[CH2:17][c:18]1[n:19][c:20](-[c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[o:27][c:28]1[CH3:29]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[c:13]1[cH:... | CCOC(=O)C(Cc1cccc2[nH]ccc12)OCC.Cc1oc(-c2ccccc2)nc1CCl | CCOC(=O)C(Cc1cccc2c1ccn2Cc1nc(-c2ccccc2)oc1C)OCC | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 558bcff26233c13696ebcbebe920e2039c7ee6d2503304edb672d21289ef564c | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(-c2nc(Cn3ccc4ccccc43)co2)cc1 | Cl-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#8;a:5]:[c:6]:1-[C;D1;H3:7].[c:8]:[c:9]1:[c:10]:[c:11]:[c:12]:[nH;D2;+0:13]:1>>[C;D1;H3:7]-[c:6]1:[#8;a:5]:[c:4]:[#7;a:3]:[c:2]:1-[CH2;D2;+0:1]-[n;H0;D3;+0:13]1:[c:12]:[c:11]:[c:10]:[c:9]:1:[c:8] | null | [] | null | null | null | null | In analogy to the procedures described in examples 1 a] and 1 b], rac-2-ethoxy-3-(1H-indol-4-yl)-propionic acid ethyl ester was reacted with 4-chloromethyl-5-methyl-2-phenyl-oxazole in N,N-dimethylformamide in the presence of sodium hydride to yield rac-2-ethoxy-3-[1-(5-methyl-2-phenyl-oxazol-4-ylmethyl)-1H-indol-4-yl]... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2[nH]ccc2c1 | c1cccc2[nH]ccc12 | c1cccc2[nH]ccc12.c1cocn1.c1ccccc1 | HCl | CN(C=O)C | null | null | CCOC(=O)C(Cc1cccc2[nH]ccc12)OCC.Cc1oc(-c2ccccc2)nc1CCl>CN(C=O)C>CCOC(=O)C(Cc1cccc2c1ccn2Cc1nc(-c2ccccc2)oc1C)OCC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8323ce15b16a4e9e9e0dc102eeab23a8 | CCOC(=O)C(Cc1cccc2[nH]ccc12)OCC.Cc1oc(-c2ccccc2F)nc1CCl>>CCOC(=O)C(Cc1cccc2c1ccn2Cc1nc(-c2ccccc2F)oc1C)OCC | C(C)OC(C(CC1=C2C=CNC2=CC=C1)OCC)=O.ClCC=1N=C(OC1C)C1=C(C=CC=C1)F.[H-].[Na+]>>C(C)OC(C(CC1=C2C=CN(C2=CC=C1)CC=1N=C(OC1C)C1=C(C=CC=C1)F)OCC)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[c:13]1[cH:14][cH:15][nH:16]2)[O:31][CH2:32][CH3:33].Cl[CH2:17][c:18]1[n:19][c:20](-[c:21]2[cH:22][cH:23][cH:24][cH:25][c:26]2[F:27])[o:28][c:29]1[CH3:30]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[c:13]... | CCOC(=O)C(Cc1cccc2[nH]ccc12)OCC.Cc1oc(-c2ccccc2F)nc1CCl | CCOC(=O)C(Cc1cccc2c1ccn2Cc1nc(-c2ccccc2F)oc1C)OCC | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 558bcff26233c13696ebcbebe920e2039c7ee6d2503304edb672d21289ef564c | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(-c2nc(Cn3ccc4ccccc43)co2)cc1 | Cl-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#8;a:5]:[c:6]:1-[C;D1;H3:7].[c:8]:[c:9]1:[c:10]:[c:11]:[c:12]:[nH;D2;+0:13]:1>>[C;D1;H3:7]-[c:6]1:[#8;a:5]:[c:4]:[#7;a:3]:[c:2]:1-[CH2;D2;+0:1]-[n;H0;D3;+0:13]1:[c:12]:[c:11]:[c:10]:[c:9]:1:[c:8] | null | [] | null | null | null | null | In analogy to the procedures described in examples 1 a] and 1 b], rac-2-ethoxy-3-(1H-indol-4-yl)-propionic acid ethyl ester was reacted with 4-chloromethyl-2-(2-fluoro-phenyl)-5-methyl-oxazole in N,N-dimethylformamide in the presence of sodium hydride to yield rac-2-ethoxy-3-{1-[2-(2-fluoro-phenyl)-5-methyl-oxazol-4-yl... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2[nH]ccc2c1 | c1cccc2[nH]ccc12 | c1cccc2[nH]ccc12.c1cocn1.c1ccccc1 | HCl | CN(C=O)C | null | null | CCOC(=O)C(Cc1cccc2[nH]ccc12)OCC.Cc1oc(-c2ccccc2F)nc1CCl>CN(C=O)C>CCOC(=O)C(Cc1cccc2c1ccn2Cc1nc(-c2ccccc2F)oc1C)OCC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6d4429bcbc7644d7a13c7f1c6da717b4 | CCOC(=O)C(Cc1cccc2[nH]ccc12)OCC.Cc1oc(-c2ccccc2Cl)nc1CCl>>CCOC(=O)C(Cc1cccc2c1ccn2Cc1nc(-c2ccccc2Cl)oc1C)OCC | C(C)OC(C(CC1=C2C=CNC2=CC=C1)OCC)=O.ClCC=1N=C(OC1C)C1=C(C=CC=C1)Cl.[H-].[Na+]>>C(C)OC(C(CC1=C2C=CN(C2=CC=C1)CC=1N=C(OC1C)C1=C(C=CC=C1)Cl)OCC)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[c:13]1[cH:14][cH:15][nH:16]2)[O:31][CH2:32][CH3:33].Cl[CH2:17][c:18]1[n:19][c:20](-[c:21]2[cH:22][cH:23][cH:24][cH:25][c:26]2[Cl:27])[o:28][c:29]1[CH3:30]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[c:13... | CCOC(=O)C(Cc1cccc2[nH]ccc12)OCC.Cc1oc(-c2ccccc2Cl)nc1CCl | CCOC(=O)C(Cc1cccc2c1ccn2Cc1nc(-c2ccccc2Cl)oc1C)OCC | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 558bcff26233c13696ebcbebe920e2039c7ee6d2503304edb672d21289ef564c | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(-c2nc(Cn3ccc4ccccc43)co2)cc1 | Cl-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#8;a:5]:[c:6]:1-[C;D1;H3:7].[c:8]:[c:9]1:[c:10]:[c:11]:[c:12]:[nH;D2;+0:13]:1>>[C;D1;H3:7]-[c:6]1:[#8;a:5]:[c:4]:[#7;a:3]:[c:2]:1-[CH2;D2;+0:1]-[n;H0;D3;+0:13]1:[c:12]:[c:11]:[c:10]:[c:9]:1:[c:8] | null | [] | null | null | null | null | In analogy to the procedures described in examples 1 a] and 1 b], rac-2-ethoxy-3-(1H-indol-4-yl)-propionic acid ethyl ester was reacted with 4-chloromethyl-2-(2-chloro-phenyl)-5-methyl-oxazole in N,N-dimethylformamide in the presence of sodium hydride to yield rac-3-{1-[2-(2-chloro-phenyl)-5-methyl-oxazol-4-ylmethyl]-1... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2[nH]ccc2c1 | c1cccc2[nH]ccc12 | c1cccc2[nH]ccc12.c1cocn1.c1ccccc1 | HCl | CN(C=O)C | null | null | CCOC(=O)C(Cc1cccc2[nH]ccc12)OCC.Cc1oc(-c2ccccc2Cl)nc1CCl>CN(C=O)C>CCOC(=O)C(Cc1cccc2c1ccn2Cc1nc(-c2ccccc2Cl)oc1C)OCC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1b6e7eb10b5f44208e4438dbf1d72dd3 | CCOC(=O)C(Cc1cccc2[nH]ccc12)OCC.Cc1ccccc1-c1nc(CCl)c(C)o1>>CCOC(=O)C(Cc1cccc2c1ccn2Cc1nc(-c2ccccc2C)oc1C)OCC | C(C)OC(C(CC1=C2C=CNC2=CC=C1)OCC)=O.ClCC=1N=C(OC1C)C1=C(C=CC=C1)C.[H-].[Na+]>>C(C)OC(C(CC1=C2C=CN(C2=CC=C1)CC=1N=C(OC1C)C1=C(C=CC=C1)C)OCC)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[c:13]1[cH:14][cH:15][nH:16]2)[O:31][CH2:32][CH3:33].Cl[CH2:17][c:18]1[n:19][c:20](-[c:21]2[cH:22][cH:23][cH:24][cH:25][c:26]2[CH3:27])[o:28][c:29]1[CH3:30]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[c:1... | CCOC(=O)C(Cc1cccc2[nH]ccc12)OCC.Cc1ccccc1-c1nc(CCl)c(C)o1 | CCOC(=O)C(Cc1cccc2c1ccn2Cc1nc(-c2ccccc2C)oc1C)OCC | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 558bcff26233c13696ebcbebe920e2039c7ee6d2503304edb672d21289ef564c | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(-c2nc(Cn3ccc4ccccc43)co2)cc1 | Cl-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#8;a:5]:[c:6]:1-[C;D1;H3:7].[c:8]:[c:9]1:[c:10]:[c:11]:[c:12]:[nH;D2;+0:13]:1>>[C;D1;H3:7]-[c:6]1:[#8;a:5]:[c:4]:[#7;a:3]:[c:2]:1-[CH2;D2;+0:1]-[n;H0;D3;+0:13]1:[c:12]:[c:11]:[c:10]:[c:9]:1:[c:8] | null | [] | null | null | null | null | In analogy to the procedures described in examples 1 a] and 1 b], rac-2-ethoxy-3-(1H-indol-4-yl)-propionic acid ethyl ester was reacted with 4-chloromethyl-5-methyl-2-o-tolyl-oxazole in N,N-dimethylformamide in the presence of sodium hydride to yield rac-2-ethoxy-3-[1-(5-methyl-2-o-tolyl-oxazol-4-ylmethyl)-1H-indol-4-y... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2[nH]ccc2c1 | c1cccc2[nH]ccc12 | c1cccc2[nH]ccc12.c1cocn1.c1ccccc1 | HCl | CN(C=O)C | null | null | CCOC(=O)C(Cc1cccc2[nH]ccc12)OCC.Cc1ccccc1-c1nc(CCl)c(C)o1>CN(C=O)C>CCOC(=O)C(Cc1cccc2c1ccn2Cc1nc(-c2ccccc2C)oc1C)OCC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1788b114ad9b4eb4a6bd3a907318d9df | CCOC(=O)C(Cc1cccc2[nH]ccc12)OCC.Cc1oc(-c2cccc(Cl)c2)nc1CCl>>CCOC(=O)C(Cc1cccc2c1ccn2Cc1nc(-c2cccc(Cl)c2)oc1C)OCC | C(C)OC(C(CC1=C2C=CNC2=CC=C1)OCC)=O.ClCC=1N=C(OC1C)C1=CC(=CC=C1)Cl.[H-].[Na+]>>C(C)OC(C(CC1=C2C=CN(C2=CC=C1)CC=1N=C(OC1C)C1=CC(=CC=C1)Cl)OCC)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[c:13]1[cH:14][cH:15][nH:16]2)[O:31][CH2:32][CH3:33].Cl[CH2:17][c:18]1[n:19][c:20](-[c:21]2[cH:22][cH:23][cH:24][c:25]([Cl:26])[cH:27]2)[o:28][c:29]1[CH3:30]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[c:... | CCOC(=O)C(Cc1cccc2[nH]ccc12)OCC.Cc1oc(-c2cccc(Cl)c2)nc1CCl | CCOC(=O)C(Cc1cccc2c1ccn2Cc1nc(-c2cccc(Cl)c2)oc1C)OCC | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 558bcff26233c13696ebcbebe920e2039c7ee6d2503304edb672d21289ef564c | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(-c2nc(Cn3ccc4ccccc43)co2)cc1 | Cl-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#8;a:5]:[c:6]:1-[C;D1;H3:7].[c:8]:[c:9]1:[c:10]:[c:11]:[c:12]:[nH;D2;+0:13]:1>>[C;D1;H3:7]-[c:6]1:[#8;a:5]:[c:4]:[#7;a:3]:[c:2]:1-[CH2;D2;+0:1]-[n;H0;D3;+0:13]1:[c:12]:[c:11]:[c:10]:[c:9]:1:[c:8] | null | [] | null | null | null | null | In analogy to the procedures described in examples 1 a] and 1 b], rac-2-ethoxy-3-(1H-indol-4-yl)-propionic acid ethyl ester was reacted with 4-chloromethyl-2-(3-chloro-phenyl)-5-methyl-oxazole in N,N-dimethylformamide in the presence of sodium hydride to yield rac-3-{1-[2-(3-chloro-phenyl)-5-methyl-oxazol-4-ylmethyl]-1... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2[nH]ccc2c1 | c1cccc2[nH]ccc12 | c1cccc2[nH]ccc12.c1cocn1.c1ccccc1 | HCl | CN(C=O)C | null | null | CCOC(=O)C(Cc1cccc2[nH]ccc12)OCC.Cc1oc(-c2cccc(Cl)c2)nc1CCl>CN(C=O)C>CCOC(=O)C(Cc1cccc2c1ccn2Cc1nc(-c2cccc(Cl)c2)oc1C)OCC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-351e9e56c9cf41e8b8365981f2334cdd | CCOC(=O)C(Cc1cccc2[nH]ccc12)OCC.Cc1oc(-c2ccc(C(F)(F)F)cc2)nc1CCl>>CCOC(=O)C(Cc1cccc2c1ccn2Cc1nc(-c2ccc(C(F)(F)F)cc2)oc1C)OCC | C(C)OC(C(CC1=C2C=CNC2=CC=C1)OCC)=O.ClCC=1N=C(OC1C)C1=CC=C(C=C1)C(F)(F)F.[H-].[Na+]>>C(C)OC(C(CC1=C2C=CN(C2=CC=C1)CC=1N=C(OC1C)C1=CC=C(C=C1)C(F)(F)F)OCC)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[c:13]1[cH:14][cH:15][nH:16]2)[O:34][CH2:35][CH3:36].Cl[CH2:17][c:18]1[n:19][c:20](-[c:21]2[cH:22][cH:23][c:24]([C:25]([F:26])([F:27])[F:28])[cH:29][cH:30]2)[o:31][c:32]1[CH3:33]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][c:8]1[cH:9][cH... | CCOC(=O)C(Cc1cccc2[nH]ccc12)OCC.Cc1oc(-c2ccc(C(F)(F)F)cc2)nc1CCl | CCOC(=O)C(Cc1cccc2c1ccn2Cc1nc(-c2ccc(C(F)(F)F)cc2)oc1C)OCC | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 558bcff26233c13696ebcbebe920e2039c7ee6d2503304edb672d21289ef564c | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(-c2nc(Cn3ccc4ccccc43)co2)cc1 | Cl-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#8;a:5]:[c:6]:1-[C;D1;H3:7].[c:8]:[c:9]1:[c:10]:[c:11]:[c:12]:[nH;D2;+0:13]:1>>[C;D1;H3:7]-[c:6]1:[#8;a:5]:[c:4]:[#7;a:3]:[c:2]:1-[CH2;D2;+0:1]-[n;H0;D3;+0:13]1:[c:12]:[c:11]:[c:10]:[c:9]:1:[c:8] | null | [] | null | null | null | null | In analogy to the procedures described in examples 1 a] and 1 b], rac-2-ethoxy-3-(1H-indol-4-yl)-propionic acid ethyl ester was reacted with 4-chloromethyl-5-methyl-2-(4-trifluoromethyl-phenyl)-oxazole in N,N-dimethylformamide in the presence of sodium hydride to yield rac-2-ethoxy-3-{1-[5-methyl-2-(4-trifluoromethyl-p... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2[nH]ccc2c1 | c1cccc2[nH]ccc12 | c1cccc2[nH]ccc12.c1cocn1.c1ccccc1 | HCl | CN(C=O)C | null | null | CCOC(=O)C(Cc1cccc2[nH]ccc12)OCC.Cc1oc(-c2ccc(C(F)(F)F)cc2)nc1CCl>CN(C=O)C>CCOC(=O)C(Cc1cccc2c1ccn2Cc1nc(-c2ccc(C(F)(F)F)cc2)oc1C)OCC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7c102c52bbbb4a23979d0e133ec9ed9e | CCOC(=O)C(Cc1cccc2[nH]ccc12)OCC.Cc1cc(-c2nc(CCl)c(C)o2)ccc1F>>CCOC(=O)C(Cc1cccc2c1ccn2Cc1nc(-c2ccc(F)c(C)c2)oc1C)OCC | C(C)OC(C(CC1=C2C=CNC2=CC=C1)OCC)=O.ClCC=1N=C(OC1C)C1=CC(=C(C=C1)F)C.[H-].[Na+]>>C(C)OC(C(CC1=C2C=CN(C2=CC=C1)CC=1N=C(OC1C)C1=CC(=C(C=C1)F)C)OCC)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[c:13]1[cH:14][cH:15][nH:16]2)[O:32][CH2:33][CH3:34].Cl[CH2:17][c:18]1[n:19][c:20](-[c:21]2[cH:22][cH:23][c:24]([F:25])[c:26]([CH3:27])[cH:28]2)[o:29][c:30]1[CH3:31]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][c:8]1[cH:9][cH:10][cH:11][c... | CCOC(=O)C(Cc1cccc2[nH]ccc12)OCC.Cc1cc(-c2nc(CCl)c(C)o2)ccc1F | CCOC(=O)C(Cc1cccc2c1ccn2Cc1nc(-c2ccc(F)c(C)c2)oc1C)OCC | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 558bcff26233c13696ebcbebe920e2039c7ee6d2503304edb672d21289ef564c | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(-c2nc(Cn3ccc4ccccc43)co2)cc1 | Cl-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#8;a:5]:[c:6]:1-[C;D1;H3:7].[c:8]:[c:9]1:[c:10]:[c:11]:[c:12]:[nH;D2;+0:13]:1>>[C;D1;H3:7]-[c:6]1:[#8;a:5]:[c:4]:[#7;a:3]:[c:2]:1-[CH2;D2;+0:1]-[n;H0;D3;+0:13]1:[c:12]:[c:11]:[c:10]:[c:9]:1:[c:8] | null | [] | null | null | null | null | In analogy to the procedures described in examples 1 a] and 1 b], rac-2-ethoxy-3-(1H-indol-4-yl)-propionic acid ethyl ester was reacted with 4-chloromethyl-2-(4-fluoro-3-methyl-phenyl)-5-methyl-oxazole in N,N-dimethylformamide in the presence of sodium hydride to yield rac-2-ethoxy-3-{1-[2-(4-fluoro-3-methyl-phenyl)-5-... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2[nH]ccc2c1 | c1cccc2[nH]ccc12 | c1cccc2[nH]ccc12.c1cocn1.c1ccccc1 | HCl | CN(C=O)C | null | null | CCOC(=O)C(Cc1cccc2[nH]ccc12)OCC.Cc1cc(-c2nc(CCl)c(C)o2)ccc1F>CN(C=O)C>CCOC(=O)C(Cc1cccc2c1ccn2Cc1nc(-c2ccc(F)c(C)c2)oc1C)OCC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7c9d2da9aa78413e9deabe8e1ce19266 | CCOC(=O)C(Cc1cccc2[nH]ccc12)OCC.Cc1oc(-c2ccc(OC(C)C)cc2)nc1CCl>>CCOC(=O)C(Cc1cccc2c1ccn2Cc1nc(-c2ccc(OC(C)C)cc2)oc1C)OCC | C(C)OC(C(CC1=C2C=CNC2=CC=C1)OCC)=O.ClCC=1N=C(OC1C)C1=CC=C(C=C1)OC(C)C.[H-].[Na+]>>C(C)OC(C(CC1=C2C=CN(C2=CC=C1)CC=1N=C(OC1C)C1=CC=C(C=C1)OC(C)C)OCC)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[c:13]1[cH:14][cH:15][nH:16]2)[O:34][CH2:35][CH3:36].Cl[CH2:17][c:18]1[n:19][c:20](-[c:21]2[cH:22][cH:23][c:24]([O:25][CH:26]([CH3:27])[CH3:28])[cH:29][cH:30]2)[o:31][c:32]1[CH3:33]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][c:8]1[cH:9]... | CCOC(=O)C(Cc1cccc2[nH]ccc12)OCC.Cc1oc(-c2ccc(OC(C)C)cc2)nc1CCl | CCOC(=O)C(Cc1cccc2c1ccn2Cc1nc(-c2ccc(OC(C)C)cc2)oc1C)OCC | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 558bcff26233c13696ebcbebe920e2039c7ee6d2503304edb672d21289ef564c | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(-c2nc(Cn3ccc4ccccc43)co2)cc1 | Cl-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#8;a:5]:[c:6]:1-[C;D1;H3:7].[c:8]:[c:9]1:[c:10]:[c:11]:[c:12]:[nH;D2;+0:13]:1>>[C;D1;H3:7]-[c:6]1:[#8;a:5]:[c:4]:[#7;a:3]:[c:2]:1-[CH2;D2;+0:1]-[n;H0;D3;+0:13]1:[c:12]:[c:11]:[c:10]:[c:9]:1:[c:8] | null | [] | null | null | null | null | In analogy to the procedures described in examples 1 a] and 1 b], rac-2-ethoxy-3-(1H-indol-4-yl)-propionic acid ethyl ester was reacted with 4-chloromethyl-2-(4-isopropoxy-phenyl)-5-methyl-oxazole in N,N-dimethylformamide in the presence of sodium hydride to yield rac-2-ethoxy-3-{1-[2-(4-isopropoxy-phenyl)-5-methyl-oxa... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2[nH]ccc2c1 | c1cccc2[nH]ccc12 | c1cccc2[nH]ccc12.c1cocn1.c1ccccc1 | HCl | CN(C=O)C | null | null | CCOC(=O)C(Cc1cccc2[nH]ccc12)OCC.Cc1oc(-c2ccc(OC(C)C)cc2)nc1CCl>CN(C=O)C>CCOC(=O)C(Cc1cccc2c1ccn2Cc1nc(-c2ccc(OC(C)C)cc2)oc1C)OCC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6a9c12be0fc447c092c1a0877ee06089 | CC(C)c1ccc(-c2nc(CCl)cs2)cc1.CCOC(=O)C(Cc1cccc2[nH]ccc12)OCC>>CCOC(=O)C(Cc1cccc2c1ccn2Cc1csc(-c2ccc(C(C)C)cc2)n1)OCC | C(C)OC(C(CC1=C2C=CNC2=CC=C1)OCC)=O.ClCC=1N=C(SC1)C1=CC=C(C=C1)C(C)C.[H-].[Na+]>>C(C)OC(C(CC1=C2C=CN(C2=CC=C1)CC=1N=C(SC1)C1=CC=C(C=C1)C(C)C)OCC)=O | Cl[CH2:17][c:18]1[cH:19][s:20][c:21](-[c:22]2[cH:23][cH:24][c:25]([CH:26]([CH3:27])[CH3:28])[cH:29][cH:30]2)[n:31]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[c:13]1[cH:14][cH:15][nH:16]2)[O:32][CH2:33][CH3:34]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][c:8]1[cH:9][cH:10][cH:11... | CC(C)c1ccc(-c2nc(CCl)cs2)cc1.CCOC(=O)C(Cc1cccc2[nH]ccc12)OCC | CCOC(=O)C(Cc1cccc2c1ccn2Cc1csc(-c2ccc(C(C)C)cc2)n1)OCC | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 558bcff26233c13696ebcbebe920e2039c7ee6d2503304edb672d21289ef564c | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(-c2nc(Cn3ccc4ccccc43)cs2)cc1 | Cl-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#16;a:5]:[c:6]:1.[c:7]:[c:8]1:[c:9]:[c:10]:[c:11]:[nH;D2;+0:12]:1>>[c:7]:[c:8]1:[c:9]:[c:10]:[c:11]:[n;H0;D3;+0:12]:1-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#16;a:5]:[c:6]:1 | null | [] | null | null | null | null | In analogy to the procedures described in examples 1 a] and 1 b], rac-2-ethoxy-3-(1H-indol-4-yl)-propionic acid ethyl ester was reacted with 4-chloromethyl-2-(4-isopropyl-phenyl)-thiazole in N,N-dimethylformamide in the presence of sodium hydride to yield rac-2-ethoxy-3-{1-[2-(4-isopropyl-phenyl)-thiazol-4-ylmethyl]-1H... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2[nH]ccc2c1 | c1cccc2[nH]ccc12 | c1cccc2[nH]ccc12.c1cscn1.c1ccccc1 | HCl | CN(C=O)C | null | null | CC(C)c1ccc(-c2nc(CCl)cs2)cc1.CCOC(=O)C(Cc1cccc2[nH]ccc12)OCC>CN(C=O)C>CCOC(=O)C(Cc1cccc2c1ccn2Cc1csc(-c2ccc(C(C)C)cc2)n1)OCC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-391b10c19c2646d59ed4c38016ccc746 | COC(=O)[C@H]1[C@@H](c2ccc(F)cc2)C[C@@H]2CC[C@H]1N2C.Cl>>Clc1ccc(C23CNCC2C3)cc1Cl | Cl.Cl.FC1=CC=C(C=C1)C(OCCN1CCN(CC1)CCCC1=CC=CC=C1)C1=CC=C(C=C1)F.C1CN(CCN1CCCC2=CC=CC=C2)CCOC(C3=CC=C(C=C3)F)C4=CC=C(C=C4)F.NCCC1=CC(O)=C(O)C=C1.CN1[C@H]2CC[C@@H]1[C@H]([C@H](C2)C3=CC=C(C=C3)F)C(=O)OC.NCCC1=CC(O)=C(O)C=C1>>Cl.ClC=1C=C(C=CC1Cl)C12CNCC2C1 | COC(=O)[C@@H:8]1[C@H]2C[CH2:10][C@H:11](N2C)[CH2:12][C@@H:7]1[c:6]1[cH:5][cH:4][c:3](F)[cH:14][cH:13]1.[ClH:15]>>[Cl:2][c:3]1[cH:4][cH:5][c:6]([C:7]23[CH2:8][NH:9][CH2:10][CH:11]2[CH2:12]3)[cH:13][c:14]1[Cl:15] | COC(=O)[C@H]1[C@@H](c2ccc(F)cc2)C[C@@H]2CC[C@H]1N2C.Cl | Clc1ccc(C23CNCC2C3)cc1Cl | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 7fd43b7a431fbe87e25671e3bad8b4d727dd63fee79d5ea69cd18958ba2bd4d8 | 7ead3674a3a97c765db7a7f941d33bc50c45ce420e8e0212173f30bd8cd7673d | c1ccc(C23CNCC2C3)cc1 | null | null | [] | null | null | null | null | The dopamine uptake transporter binding assay was performed according to the methods described in Madras et al., 1989, Mol. Pharmacol. 36(4):518–524 and Javitch et al., 1984, Mol. Pharmacol. 26(1):35–44. The receptor source was guinea pig striatal membranes; the radioligand was [3H]WIN 35,428 (DuPont-NEN, Boston, Mass.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Tertiary amine | Aromatic halide.Aromatic halide.Secondary amine | C1C[C@@H]2CC[C@H](C1)N2.c1ccccc1 | c1ccccc1.C1NCC2CC12 | c1ccccc1.C1NCC2CC12 | HF | null | null | null | COC(=O)[C@H]1[C@@H](c2ccc(F)cc2)C[C@@H]2CC[C@H]1N2C.Cl>>Clc1ccc(C23CNCC2C3)cc1Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-25f95517642f49208b1291046c1ef585 | CCI.O=S(=O)(c1ccccc1)n1ccc2cc(Cl)ccc21>>CCc1cc2cc(Cl)ccc2n1S(=O)(=O)c1ccccc1 | [Li]C(C)(C)C.C1(=CC=CC=C1)S(=O)(=O)N1C=CC2=CC(=CC=C12)Cl.C(C)I>>C1(=CC=CC=C1)S(=O)(=O)N1C(=CC2=CC(=CC=C12)Cl)CC | I[CH2:2][CH3:1].[cH:3]1[cH:4][c:5]2[cH:6][c:7]([Cl:8])[cH:9][cH:10][c:11]2[n:12]1[S:13](=[O:14])(=[O:15])[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1>>[CH3:1][CH2:2][c:3]1[cH:4][c:5]2[cH:6][c:7]([Cl:8])[cH:9][cH:10][c:11]2[n:12]1[S:13](=[O:14])(=[O:15])[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1 | CCI.O=S(=O)(c1ccccc1)n1ccc2cc(Cl)ccc21 | CCc1cc2cc(Cl)ccc2n1S(=O)(=O)c1ccccc1 | null | null | C1CCOC1 | C-C Coupling | Friedel-Crafts alkylation with halide | 4d207e3c16b48cdb1b200abcc5d949fb598eca99a1ea70eadeb1706cdf73ce8c | f5e5e22797736d188bba28deb76a4cee8e4fee4dca04fe24f733d2ee68a23361 | O=S(=O)(c1ccccc1)n1ccc2ccccc21 | I-[CH2;D2;+0:1]-[C;D1;H3:2].[#16:3]-[#7;a:4]1:[c:5]:[c:6]:[c:7]:[cH;D2;+0:8]:1>>[#16:3]-[#7;a:4]1:[c:5]:[c:6]:[c:7]:[c;H0;D3;+0:8]:1-[CH2;D2;+0:1]-[C;D1;H3:2] | null | [] | null | null | 15 | MINUTE | t-BuLi (3.7 mL of 1.7 M solution in pentane) was added dropwise to a solution of N-(benzensulfonyl)-5-chloroindole (1) (J. Org. Chem. 1981, 46, 3859) (1.5 g, 5.14 mmol) in THF (35 mL) at −70° C., under a nitrogen atmosphere. The mixture was stirred for 15 min, allowed to warm to room temperature over 20 min, cooled to ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccccc1 | HI | C1CCOC1 | null | 0.25 | CCI.O=S(=O)(c1ccccc1)n1ccc2cc(Cl)ccc21>C1CCOC1>CCc1cc2cc(Cl)ccc2n1S(=O)(=O)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6eb7296ff68e46c49fe21f7b0425c303 | CCc1cc2cc(Cl)ccc2n1S(=O)(=O)c1ccccc1>>CCc1cc2cc(Cl)ccc2[nH]1 | C1(=CC=CC=C1)S(=O)(=O)N1C(=CC2=CC(=CC=C12)Cl)CC.[OH-].[Na+]>>ClC=1C=C2C=C(NC2=CC1)CC | O=S(=O)(c1ccccc1)[n:12]1[c:3]([CH2:2][CH3:1])[cH:4][c:5]2[cH:6][c:7]([Cl:8])[cH:9][cH:10][c:11]21>>[CH3:1][CH2:2][c:3]1[cH:4][c:5]2[cH:6][c:7]([Cl:8])[cH:9][cH:10][c:11]2[nH:12]1 | CCc1cc2cc(Cl)ccc2n1S(=O)(=O)c1ccccc1 | CCc1cc2cc(Cl)ccc2[nH]1 | null | null | CO | Reduction | OtherReaction | 0bdc206bc82b142c1f26c470803f0ffa0113e205282144abd9f91e21be64ca57 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | c1ccc2[nH]ccc2c1 | O=S(=O)(-[n;H0;D3;+0:1]1:[c:2](:[c:3]):[c:4]:[c:5]:[c:6]:1-[C:7])-c1:c:c:c:c:c:1>>[C:7]-[c:6]1:[c:5]:[c:4]:[c:2](:[c:3]):[nH;D2;+0:1]:1 | null | [] | null | null | null | null | A mixture of 2 (1.3 g, 4.07 mmol), 2N NaOH (12 mL), and MeOH (62 mL) was refluxed for 40 h. The organic solvent was evaporated and the remaining residue was extracted with EtOAc. The combined extract were washed with brine, dried (Na2SO4) and evaporated in vacuo to give a residue which was purified by flash chromatogra... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | HO- | CO | null | null | CCc1cc2cc(Cl)ccc2n1S(=O)(=O)c1ccccc1>CO>CCc1cc2cc(Cl)ccc2[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fd5736776b90490195ef7a703ff54b79 | CCc1cc2cc(Cl)ccc2[nH]1.CN(C)C=C[N+](=O)[O-]>>CCc1[nH]c2ccc(Cl)cc2c1/C=C/[N+](=O)[O-] | ClC=1C=C2C=C(NC2=CC1)CC.CN(C=C[N+](=O)[O-])C>>ClC=1C=C2C(=C(NC2=CC1)CC)\C=C\[N+](=O)[O-] | [CH3:1][CH2:2][c:3]1[nH:4][c:5]2[cH:6][cH:7][c:8]([Cl:9])[cH:10][c:11]2[cH:12]1.CN(C)[CH:13]=[CH:14][N+:15](=[O:16])[O-:17]>>[CH3:1][CH2:2][c:3]1[nH:4][c:5]2[cH:6][cH:7][c:8]([Cl:9])[cH:10][c:11]2[c:12]1/[CH:13]=[CH:14]/[N+:15](=[O:16])[O-:17] | CCc1cc2cc(Cl)ccc2[nH]1.CN(C)C=C[N+](=O)[O-] | CCc1[nH]c2ccc(Cl)cc2c1/C=C/[N+](=O)[O-] | null | null | CCOC(=O)C.CCOCC.FC(C(=O)O)(F)F | C-C Coupling | OtherReaction | c3227f40c2543cc995070ba4cbbb09381453193b91b46918c9443f6134d795df | dc0a4ab4f14a00c6fba06e41fb1b6f83f79790d1b6c10447a4a10f352f15c219 | c1ccc2[nH]ccc2c1 | C-N(-C)-[CH;D2;+0:1]=[C:2]-[#7;+:3].[C:4]-[c:5]1:[#7;a:6]:[c:7](:[c:8]):[c:9](:[c:10]):[cH;D2;+0:11]:1>>[#7;+:3]/[C:2]=[CH;D2;+0:1]/[c;H0;D3;+0:11]1:[c:9](:[c:10]):[c:7](:[c:8]):[#7;a:6]:[c:5]:1-[C:4] | null | [] | null | null | 0.5 | HOUR | The indole 3 (5 mmol) was added to a stirred ice-cooled solution of 1-(dimethylamino)-2-nitroethylene (0.58 g, 5 mmol) in trifluoroacetic acid (5 mL). The mixture was stirred at room temperature under N2, for 0.5 h and then poured onto ice water. The aqueous solution was extracted with ethyl acetate, the combined organ... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Enamine | Enamine | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | Other | CCOC(=O)C.CCOCC.FC(C(=O)O)(F)F | null | 0.5 | CCc1cc2cc(Cl)ccc2[nH]1.CN(C)C=C[N+](=O)[O-]>CCOC(=O)C.CCOCC.FC(C(=O)O)(F)F>CCc1[nH]c2ccc(Cl)cc2c1/C=C/[N+](=O)[O-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-07f7b555c74944509c2041118cd716bb | C=O.CCc1[nH]c2ccc(Cl)cc2c1CCN>>CCc1[nH]c2ccc(Cl)cc2c1CCN(C)C | C(=O)([O-])[O-].[K+].[K+].ClC1=CC=C2NC(=C(CCN)C2=C1)CC.C(#N)[BH3-].[Na+].C=O>>ClC1=CC=C2NC(=C(CCN(C)C)C2=C1)CC | O=[CH2:16].[CH3:1][CH2:2][c:3]1[nH:4][c:5]2[cH:6][cH:7][c:8]([Cl:9])[cH:10][c:11]2[c:12]1[CH2:13][CH2:14][NH2:15]>>[CH3:1][CH2:2][c:3]1[nH:4][c:5]2[cH:6][cH:7][c:8]([Cl:9])[cH:10][c:11]2[c:12]1[CH2:13][CH2:14][N:15]([CH3:16])[CH3:17] | C=O.CCc1[nH]c2ccc(Cl)cc2c1CCN | CCc1[nH]c2ccc(Cl)cc2c1CCN(C)C | null | null | CO.CC(=O)O | Heteroatom Alkylation and Arylation | Eschweiler-Clarke Primary Amine Methylation | 5bc40be4d4b4346801fbfcec480fec37de3ff2eecebe2990b3686fa4792d12b6 | 5cdbf447f632627824e84e0bcac2293ea9ebd70c19b0d56dea90691653b444c7 | c1ccc2[nH]ccc2c1 | O=[CH2;D1;+0:1].[C:2]-[C:3]-[NH2;D1;+0:4]>>[C:2]-[C:3]-[N;H0;D3;+0:4](-[C;D1;H3:5])-[CH3;D1;+0:1] | null | [] | 25 | CELSIUS | 2.5 | HOUR | 40% HCHO (0.95 mL) in MeOH (16 mL) was added dropwise to a stirred cooled (0° C.) solution of (5) (3.16 mmol), AcOH (0.47 mL) and sodium cyanoborohydride (0.35 g). The resulting mixture was allowed to stir at 25° C. for 2.5 h. A saturated aqueous solution of K2CO3 (5 mL) was added, MeOH was removed in vacuo and the aqu... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Primary amine | Tertiary amine | null | null | c1ccc2[nH]ccc2c1 | null | CO.CC(=O)O | 25 | 2.5 | C=O.CCc1[nH]c2ccc(Cl)cc2c1CCN>CO.CC(=O)O>CCc1[nH]c2ccc(Cl)cc2c1CCN(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b28a894c0a8745c8aa52e46ff1d2c3dd | Cc1cc2c(C#C[Si](C)(C)C)cccc2n1C(=O)OC(C)(C)C.OO>>Cc1cc2c(CC(=O)O)cccc2n1C(=O)OC(C)(C)C | C(C)(C)(C)OC(=O)N1C(=CC2=C(C=CC=C12)C#C[Si](C)(C)C)C.[OH-].[Na+].OO.C1CCCCC1>>C(C)(C)(C)OC(=O)N1C(=CC=2C(=CC=CC12)CC(=O)O)C | C[Si](C)(C)[C:7]#[C:6][c:5]1[c:4]2[cH:3][c:2]([CH3:1])[n:14]([C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[c:13]2[cH:12][cH:11][cH:10]1.[OH:8][OH:9]>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([CH2:6][C:7](=[O:8])[OH:9])[cH:10][cH:11][cH:12][c:13]2[n:14]1[C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21] | Cc1cc2c(C#C[Si](C)(C)C)cccc2n1C(=O)OC(C)(C)C.OO | Cc1cc2c(CC(=O)O)cccc2n1C(=O)OC(C)(C)C | null | null | O1CCCC1 | Acylation | OtherReaction | aae3708f4ab12985bc7e7792b4d5a940099c7c4e54760b6b09f5515213d5fdd5 | 8648db698489f4ab5a11896e8f25622be863bfd266e8e7e2f21a2f6691197ae8 | c1ccc2[nH]ccc2c1 | C-[Si](-C)(-C)-[C;H0;D2;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5]:[c:6]:[#7;a:7].[OH;D1;+0:8]-[OH;D1;+0:9]>>[#7;a:7]:[c:6]:[c:5]:[c:3](-[CH2;D2;+0:2]-[C;H0;D3;+0:1](=[O;H0;D1;+0:8])-[OH;D1;+0:9]):[c:4] | null | [] | 0 | CELSIUS | 1 | HOUR | A solution of cyclohexane (16.1 ml) in tetrahydrofuran (160 ml) was cooled at −10° C., and then to the mixture was added dropwise borane-tetrahydrofuran complex (1M, 80 ml), and the mixture was stirred at 0° C. for 1 hour. To the solution was added dropwise a solution of 1-t-butoxycarbonyl-2-methyl-4-(2-trimethylsilyle... | 10.6084/m9.figshare.5104873.v1 | null | Peroxide.Alkyne.Silyl protective group | Carboxylic acid | null | null | c1cc2ccccc2[nH]1 | Other | O1CCCC1 | 0 | 1 | Cc1cc2c(C#C[Si](C)(C)C)cccc2n1C(=O)OC(C)(C)C.OO>O1CCCC1>Cc1cc2c(CC(=O)O)cccc2n1C(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c174ab2d22d7462da09df0f9e3a20ca3 | Cc1cc2c(CC(=O)O)cccc2n1C(=O)OC(C)(C)C>>Cc1cc2c(CC(=O)O)cccc2[nH]1 | [OH-].[Na+].C(C)(C)(C)OC(=O)N1C(=CC=2C(=CC=CC12)CC(=O)O)C.O>>CC=1NC=2C=CC=C(C2C1)CC(=O)O | CC(C)(C)OC(=O)[n:14]1[c:2]([CH3:1])[cH:3][c:4]2[c:5]([CH2:6][C:7](=[O:8])[OH:9])[cH:10][cH:11][cH:12][c:13]21>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([CH2:6][C:7](=[O:8])[OH:9])[cH:10][cH:11][cH:12][c:13]2[nH:14]1 | Cc1cc2c(CC(=O)O)cccc2n1C(=O)OC(C)(C)C | Cc1cc2c(CC(=O)O)cccc2[nH]1 | null | null | CO | Reduction | Boc amine deprotection | eefd4487d640b2607d7a60d065f8822bc457add01d643b9dbf7d76d9b4bfeca6 | e1bf5a54b1f87284564f107662531aec2aff7de801e4606340967b38924afb28 | c1ccc2[nH]ccc2c1 | C-C(-C)(-C)-O-C(=O)-[n;H0;D3;+0:1]1:[c:2](:[c:3]):[c:4]:[c:5]:[c:6]:1-[C;D1;H3:7]>>[C;D1;H3:7]-[c:6]1:[c:5]:[c:4]:[c:2](:[c:3]):[nH;D2;+0:1]:1 | 85.6 | [{"value": 85.6, "product": "CC=1NC=2C=CC=C(C2C1)CC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 3 | HOUR | To a mixture of 1-t-butoxycarbonyl-2-methylindole-4-acetic acid (96.3 g) in methanol (200 ml)-water (100 ml) was added dropwise 5N aqueous solution of sodium hydroxide (200 ml) at room temperature, and the mixture was stirred at 50° C. for 3 hours and then stirred at room temperature for 12 hours. The reaction mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Boc | null | c1cc2ccccc2[nH]1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | HO- | CO | 50 | 3 | Cc1cc2c(CC(=O)O)cccc2n1C(=O)OC(C)(C)C>CO>Cc1cc2c(CC(=O)O)cccc2[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-77ba0c26a98b4db29c2df9d240301f25 | C=CCBr.Cc1cc2c(CC(=O)O)cccc2[nH]1>>C=CCOC(=O)Cc1cccc2[nH]c(C)cc12 | Cl.C(C)(=O)OCC.C([O-])([O-])=O.[K+].[K+].CC=1NC=2C=CC=C(C2C1)CC(=O)O.C(C=C)Br>>C(C=C)OC(CC=1C=2C=C(NC2C=CC1)C)=O | Br[CH2:3][CH:2]=[CH2:1].[OH:4][C:5](=[O:6])[CH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[nH:13][c:14]([CH3:15])[cH:16][c:17]12>>[CH2:1]=[CH:2][CH2:3][O:4][C:5](=[O:6])[CH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[nH:13][c:14]([CH3:15])[cH:16][c:17]12 | C=CCBr.Cc1cc2c(CC(=O)O)cccc2[nH]1 | C=CCOC(=O)Cc1cccc2[nH]c(C)cc12 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 06c4f868ad4646eea8208ecb83f54ca035dd62d04f0d8101641a4f487f2c695c | 8446834f0edd1e71a2dcaffc09b80c7367abf3407263a8998354a2d20c1766bb | c1ccc2[nH]ccc2c1 | Br-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3].[C:4]-[C:5](=[O;D1;H0:6])-[OH;D1;+0:7]>>[C:4]-[C:5](=[O;D1;H0:6])-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3] | null | [] | 50 | CELSIUS | 1 | HOUR | To a solution of 2-methylindole-4-acetic acid (53 g) in N,N-dimethylformamide (500 ml) was added dropwise allyl bromide (31 ml), and added anhydrous potassium carbonate (59 g). The mixture was stirred at 50° C. for 1 hour. After cooling to room temperature, the reaction mixture was poured into a mixture of 2N hydrochlo... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid | Ester | null | null | c1ccc2[nH]ccc2c1 | HBr | CN(C=O)C | 50 | 1 | C=CCBr.Cc1cc2c(CC(=O)O)cccc2[nH]1>CN(C=O)C>C=CCOC(=O)Cc1cccc2[nH]c(C)cc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4cc1be09091443928f00b584eef1d8bf | CCCOCCCl.O=C(O)c1ccc(O)cc1>>CCCOCCOc1ccc(C(=O)O)cc1 | O.OC1=CC=C(C(=O)O)C=C1.C([O-])([O-])=O.[K+].[K+].C(CC)OCCCl>>C(CC)OCCOC1=CC=C(C(=O)O)C=C1 | Cl[CH2:6][CH2:5][O:4][CH2:3][CH2:2][CH3:1].[OH:7][c:8]1[cH:9][cH:10][c:11]([C:12](=[O:13])[OH:14])[cH:15][cH:16]1>>[CH3:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]([C:12](=[O:13])[OH:14])[cH:15][cH:16]1 | CCCOCCCl.O=C(O)c1ccc(O)cc1 | CCCOCCOc1ccc(C(=O)O)cc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2]-[#8:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 105.6 | [{"value": 105.6, "product": "C(CC)OCCOC1=CC=C(C(=O)O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 4-hydroxybenzoic acid (3.04 g) and anhydrous potassium carbonate (5.52 g) in N,N-dimethylformamide (20 ml) was added 2-propyloxyethyl chloride (2.94 g), and the mixture was stirred at room temperature overnight, and then stirred at 80° C. for 8 hours. To a reaction solution was added water, and then th... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HCl | CN(C=O)C | null | 8 | CCCOCCCl.O=C(O)c1ccc(O)cc1>CN(C=O)C>CCCOCCOc1ccc(C(=O)O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0da4b96c7f31489a97331b969fe85f03 | CCCOCCOc1ccc(C(=O)n2c(C)cc3c(CC(=O)O)cccc32)cc1.[C]=O>>COC(=O)c1cccc2[nH]c(C)cc12 | [C]=O.C(CC)OCCOC1=CC=C(C(=O)N2C(=CC=3C(=CC=CC23)CC(=O)O)C)C=C1.CN(C=O)C.C(C)N(CC)CC>>COC(=O)C=1C=2C=C(NC2C=CC1)C | CCCOCCOc1ccc(C(=O)[n:10]2[c:9]3[cH:8][cH:7][cH:6][c:5]([CH2:3]C(O)=[O:4])[c:14]3[cH:13][c:11]2[CH3:12])cc1.[C:1]=[O:2]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]2[nH:10][c:11]([CH3:12])[cH:13][c:14]12 | CCCOCCOc1ccc(C(=O)n2c(C)cc3c(CC(=O)O)cccc32)cc1.[C]=O | COC(=O)c1cccc2[nH]c(C)cc12 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | CO.O.C(C)(=O)OCC | Acylation | OtherReaction | c4d7db8d861eccc4eef0f45dc01a46d968a27923a9a03a47d2fffe9b6f288515 | 3140e6b32004c2b2ca7fe186fe4fada9a4f8cb455d6be3beb776bef0dfdf7fed | c1ccc2[nH]ccc2c1 | C-C-C-O-C-C-O-c1:c:c:c(-C(=O)-[n;H0;D3;+0:1]2:[c:2](-[C;D1;H3:3]):[c:4]:[c:5](:[c:6](-[CH2;D2;+0:7]-C(-O)=[O;H0;D1;+0:8]):[c:9]):[c:10]:2:[c:11]):c:c:1.[C;H0;D1;+0:12]=[O;H0;D1;+0:13]>>[C;D1;H3:3]-[c:2]1:[c:4]:[c:5](:[c:6](-[C;H0;D3;+0:7](=[O;H0;D1;+0:8])-[O;H0;D2;+0:13]-[CH3;D1;+0:12]):[c:9]):[c:10](:[c:11]):[nH;D2;+0... | null | [] | 60 | CELSIUS | 8 | HOUR | To a solution of 2-methyl-4-trifluoromethanesulfoxyindole (6.32 g; prepared in Reference Example 1) in methanol (33.43 ml)-N,N-dimethylformamide (200 ml) was added triethylamine (6.3 ml) and tetrakis(triphenylphosphine)palladium (2.6 g). The inside of the vessel was replaced with carbon monoxide and the mixture was sti... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ether.Ether | Ester | c1ccccc1.c1cc2ccccc2[nH]1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | HO- | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.CO.O.C(C)(=O)OCC | 60 | 8 | CCCOCCOc1ccc(C(=O)n2c(C)cc3c(CC(=O)O)cccc32)cc1.[C]=O>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.CO.O.C(C)(=O)OCC>COC(=O)c1cccc2[nH]c(C)cc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e966145aa40f4b01849c2a2a0a2e9290 | COC(=O)c1cccc2[nH]c(C)cc12>>Cc1cc2c(C(=O)O)cccc2[nH]1 | COC(=O)C=1C=2C=C(NC2C=CC1)C.Cl>>CC=1NC=2C=CC=C(C2C1)C(=O)O | C[O:8][C:6]([c:5]1[c:4]2[cH:3][c:2]([CH3:1])[nH:13][c:12]2[cH:11][cH:10][cH:9]1)=[O:7]>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([C:6](=[O:7])[OH:8])[cH:9][cH:10][cH:11][c:12]2[nH:13]1 | COC(=O)c1cccc2[nH]c(C)cc12 | Cc1cc2c(C(=O)O)cccc2[nH]1 | null | null | [OH-].[Na+] | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc2[nH]ccc2c1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | 40.2 | [{"value": 40.2, "product": "CC=1NC=2C=CC=C(C2C1)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 8 | HOUR | To a solution of 2-methylindole-4-carboxylic acid methyl ester (4.3 g; prepared in Reference Example 9) in methanol-dioxane (10 ml+10 ml) was added 5N aqueous solution of sodium hydroxide (10 ml), and the mixture was stirred at 60° C. overnight. To the reaction solution was added 2N hydrochloric acid, and then extracte... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccc2[nH]ccc2c1 | Other | [OH-].[Na+] | 60 | 8 | COC(=O)c1cccc2[nH]c(C)cc12>[OH-].[Na+]>Cc1cc2c(C(=O)O)cccc2[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8816db2c05c24d459c479b80e73fd217 | BrCc1ccccc1.Cc1cc2c(C(=O)O)cccc2[nH]1>>Cc1cc2c(C(=O)OCc3ccccc3)cccc2[nH]1 | O.CC=1NC=2C=CC=C(C2C1)C(=O)O.C([O-])([O-])=O.[K+].[K+].C(C1=CC=CC=C1)Br>>C(C1=CC=CC=C1)OC(=O)C=1C=2C=C(NC2C=CC1)C | Br[CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1.[CH3:1][c:2]1[cH:3][c:4]2[c:5]([C:6](=[O:7])[OH:8])[cH:16][cH:17][cH:18][c:19]2[nH:20]1>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([C:6](=[O:7])[O:8][CH2:9][c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)[cH:16][cH:17][cH:18][c:19]2[nH:20]1 | BrCc1ccccc1.Cc1cc2c(C(=O)O)cccc2[nH]1 | Cc1cc2c(C(=O)OCc3ccccc3)cccc2[nH]1 | null | null | CN(C=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 06c4f868ad4646eea8208ecb83f54ca035dd62d04f0d8101641a4f487f2c695c | 8446834f0edd1e71a2dcaffc09b80c7367abf3407263a8998354a2d20c1766bb | O=C(OCc1ccccc1)c1cccc2[nH]ccc12 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6](-[OH;D1;+0:7])-[c:8]>>[O;D1;H0:5]=[C:6](-[c:8])-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 80 | CELSIUS | 2 | HOUR | To a solution of 2-methylindole-4-carboxylic acid (690 mg; prepared in Reference Example 10) in N,N-dimethylformamide (10 ml) was added anhydrous potassium carbonate (815 mg) and benzyl bromide (0.7 ml) at room temperature, and the mixture was stirred at 80° C. for 2 hours. To the reaction solution was added water and ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid | Ester | null | null | c1ccccc1.c1ccc2[nH]ccc2c1 | HBr | CN(C=O)C.C(C)(=O)OCC | 80 | 2 | BrCc1ccccc1.Cc1cc2c(C(=O)O)cccc2[nH]1>CN(C=O)C.C(C)(=O)OCC>Cc1cc2c(C(=O)OCc3ccccc3)cccc2[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9c82ce6bb1624d23822093bef6f2b185 | CCCCOc1ccc(C(=O)Cl)cc1.Cc1cc2c(C(=O)OCc3ccccc3)cccc2[nH]1>>CCCCOc1ccc(C(=O)n2c(C)cc3c(C(=O)OCc4ccccc4)cccc32)cc1 | C(CCC)OC1=CC=C(C(=O)Cl)C=C1.O.C(C1=CC=CC=C1)OC(=O)C=1C=2C=C(NC2C=CC1)C.[H-].[Na+]>>C(C1=CC=CC=C1)OC(=O)C=1C=2C=C(N(C2C=CC1)C(C1=CC=C(C=C1)OCCCC)=O)C | Cl[C:10]([c:9]1[cH:8][cH:7][c:6]([O:5][CH2:4][CH2:3][CH2:2][CH3:1])[cH:33][cH:32]1)=[O:11].[nH:12]1[c:13]([CH3:14])[cH:15][c:16]2[c:17]([C:18](=[O:19])[O:20][CH2:21][c:22]3[cH:23][cH:24][cH:25][cH:26][cH:27]3)[cH:28][cH:29][cH:30][c:31]12>>[CH3:1][CH2:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]([C:10](=[O:11])[n:12]2[... | CCCCOc1ccc(C(=O)Cl)cc1.Cc1cc2c(C(=O)OCc3ccccc3)cccc2[nH]1 | CCCCOc1ccc(C(=O)n2c(C)cc3c(C(=O)OCc4ccccc4)cccc32)cc1 | null | null | CN(C=O)C.C(C)(=O)OCC | Acylation | N-alkylation of secondary amines with alkyl halides | 2516cb117ae5788695cb83bfff0c334b0906c10fe9691085b1dd434be49735ca | edbcca52d877d662e04f0d6de1a7107a8eca1d366ee6da0d92e37eb02a291876 | O=C(OCc1ccccc1)c1cccc2c1ccn2C(=O)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[c:7]1:[c:8]:[c:9]:[c:10](:[c:11]):[nH;D2;+0:12]:1>>[C;D1;H3:6]-[c:7]1:[c:8]:[c:9]:[c:10](:[c:11]):[n;H0;D3;+0:12]:1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 30 | MINUTE | To a solution of 2-methyindole-4-carboxylic acid benzyl ester (690 mg; prepared in Reference Example 11) in N,N-dimethylformamide (8 ml) was added sodium hydride (114 mg; 60%) at 0° C., and the mixture was stirred at the same temperature for 30 minutes. To the reaction mixture was added 4-butoxybenzoyl chloride (0.54 m... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | null | c1ccc2[nH]ccc2c1 | c1cc2ccccc2[nH]1 | c1ccccc1.c1ccccc1.c1cc2ccccc2[nH]1 | HCl | CN(C=O)C.C(C)(=O)OCC | null | 0.5 | CCCCOc1ccc(C(=O)Cl)cc1.Cc1cc2c(C(=O)OCc3ccccc3)cccc2[nH]1>CN(C=O)C.C(C)(=O)OCC>CCCCOc1ccc(C(=O)n2c(C)cc3c(C(=O)OCc4ccccc4)cccc32)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6639fcbb31a44145a65a3054f940eb48 | COC(=O)CBr.Cc1cc2c(O)cccc2[nH]1>>COC(=O)C(C)Oc1cccc2[nH]ccc12 | O.CC=1NC2=CC=CC(=C2C1)O.C([O-])([O-])=O.[K+].[K+].BrCC(=O)OC>>COC(C(C)OC1=C2C=CNC2=CC=C1)=O | Br[CH2:5][C:3]([O:2][CH3:1])=[O:4].[CH3:6][c:14]1[nH:13][c:12]2[cH:11][cH:10][cH:9][c:8]([OH:7])[c:16]2[cH:15]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH3:6])[O:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[nH:13][cH:14][cH:15][c:16]12 | COC(=O)CBr.Cc1cc2c(O)cccc2[nH]1 | COC(=O)C(C)Oc1cccc2[nH]ccc12 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 87eb94b283b9f6681e1eaee0d66abd368cd4d2be829013c2f118b9b3cc5bcb59 | 0865de4e1853c59ac25437e36fd18b03329566cb9eff4b4f0ce70d5714692fd3 | c1ccc2[nH]ccc2c1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5].[CH3;D1;+0:6]-[c;H0;D3;+0:7]1:[#7;a:8]:[c:9]:[c:10](:[c:11]:1):[c:12](-[OH;D1;+0:13]):[c:14]>>[C;D1;H3:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH;D3;+0:1](-[CH3;D1;+0:6])-[O;H0;D2;+0:13]-[c:12](:[c:14]):[c:10]1:[c:9]:[#7;a:8]:[cH;D2;+0:7]:[c:11]:1 | null | [] | 80 | CELSIUS | 2 | HOUR | To a solution of 2-methyl-4-hydroxyindole (5 g) in N,N-dimethylformamide (50 ml) was added anhydrous potassium carbonate 11.7 g) and methyl bromoacetate (3.54 ml) at room temperature, and the mixture was stirred at 80° C. for 2 hours. To the reaction solution was added iced water to give the title compound (5.4 g) havi... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Ester.Ether | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | HBr | CN(C=O)C | 80 | 2 | COC(=O)CBr.Cc1cc2c(O)cccc2[nH]1>CN(C=O)C>COC(=O)C(C)Oc1cccc2[nH]ccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9780cbde62544c4190fa07986e5ceffd | COC(=O)C(C)Oc1cccc2[nH]ccc12>>CC(Oc1cccc2[nH]ccc12)C(=O)O | COC(C(C)OC1=C2C=CNC2=CC=C1)=O.O1CCOCC1.[OH-].[Na+].Cl>>CC(C(=O)O)OC1=C2C=CNC2=CC=C1 | C[O:15][C:13]([CH:2]([CH3:1])[O:3][c:4]1[cH:5][cH:6][cH:7][c:8]2[nH:9][cH:10][cH:11][c:12]12)=[O:14]>>[CH3:1][CH:2]([O:3][c:4]1[cH:5][cH:6][cH:7][c:8]2[nH:9][cH:10][cH:11][c:12]12)[C:13](=[O:14])[OH:15] | COC(=O)C(C)Oc1cccc2[nH]ccc12 | CC(Oc1cccc2[nH]ccc12)C(=O)O | null | null | CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc2[nH]ccc2c1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 69.2 | [{"value": 69.2, "product": "CC(C(=O)O)OC1=C2C=CNC2=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 2-methylindol-4-yloxyacetic acid methyl ester (5.4 g) in methanol (18 ml)—dioxane (36 ml) was added 5N aqueous solution of sodium hydroxide (15 ml), and the mixture was stirred at room temperature for 1 hour. To the reaction solution was added 2N hydrochloric acid to give the title compound (3.5 g) hav... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccc2[nH]ccc2c1 | Other | CO | null | 1 | COC(=O)C(C)Oc1cccc2[nH]ccc12>CO>CC(Oc1cccc2[nH]ccc12)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6a02d285179643be84a2f1e9dba40b37 | C=CCBr.CC(Oc1cccc2[nH]ccc12)C(=O)O>>C=CCOC(=O)C(C)Oc1cccc2[nH]ccc12 | O.CC(C(=O)O)OC1=C2C=CNC2=CC=C1.C([O-])([O-])=O.[K+].[K+].C(C=C)Br>>C(C=C)OC(C(C)OC1=C2C=CNC2=CC=C1)=O | Br[CH2:3][CH:2]=[CH2:1].[OH:4][C:5](=[O:6])[CH:7]([CH3:8])[O:9][c:10]1[cH:11][cH:12][cH:13][c:14]2[nH:15][cH:16][cH:17][c:18]12>>[CH2:1]=[CH:2][CH2:3][O:4][C:5](=[O:6])[CH:7]([CH3:8])[O:9][c:10]1[cH:11][cH:12][cH:13][c:14]2[nH:15][cH:16][cH:17][c:18]12 | C=CCBr.CC(Oc1cccc2[nH]ccc12)C(=O)O | C=CCOC(=O)C(C)Oc1cccc2[nH]ccc12 | null | null | CN(C=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 06c4f868ad4646eea8208ecb83f54ca035dd62d04f0d8101641a4f487f2c695c | 8446834f0edd1e71a2dcaffc09b80c7367abf3407263a8998354a2d20c1766bb | c1ccc2[nH]ccc2c1 | Br-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3].[C:4]-[C:5](=[O;D1;H0:6])-[OH;D1;+0:7]>>[C:4]-[C:5](=[O;D1;H0:6])-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3] | null | [] | 80 | CELSIUS | 2 | HOUR | To a solution of 2-methylindol-4-yloxyacetic acid (2 g) in N,N-dimethylformamide (20 ml) was added anhydrous potassium carbonate (2.02 g) and allyl bromide (1.27 ml), and the mixture was stirred at 80° C. for 2 hours. To the reaction mixture was added water and ethyl acetate, then separated. The aqueous layer was extra... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid | Ester | null | null | c1ccc2[nH]ccc2c1 | HBr | CN(C=O)C.C(C)(=O)OCC | 80 | 2 | C=CCBr.CC(Oc1cccc2[nH]ccc12)C(=O)O>CN(C=O)C.C(C)(=O)OCC>C=CCOC(=O)C(C)Oc1cccc2[nH]ccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1894c7f70c5c4391b585a4d47e964011 | C=CC(=O)OC.Cc1[nH]c2cccc(C(F)(F)F)c2c1OS(=O)(=O)O>>COC(=O)C=Cc1cccc2[nH]c(C)cc12 | O.CC=1NC2=CC=CC(=C2C1OS(=O)(=O)O)C(F)(F)F.COC(C=C)=O.C(C)(C)N(CC)C(C)C>>COC(C=CC1=C2C=C(NC2=CC=C1)C)=O | [CH3:1][O:2][C:3](=[O:4])[CH:5]=[CH2:6].O=S(=O)(O)O[c:15]1[c:13]([CH3:14])[nH:12][c:11]2[cH:10][cH:9][cH:8][c:7](C(F)(F)F)[c:16]21>>[CH3:1][O:2][C:3](=[O:4])[CH:5]=[CH:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[nH:12][c:13]([CH3:14])[cH:15][c:16]12 | C=CC(=O)OC.Cc1[nH]c2cccc(C(F)(F)F)c2c1OS(=O)(=O)O | COC(=O)C=Cc1cccc2[nH]c(C)cc12 | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | CN(C=O)C.C(C)(=O)OCC | C-C Coupling | OtherReaction | dbd7bd3a31a228231dfa53765efe53245ac85efb75c66735946cda27d559f7ca | 0f707190f28e15d1f37405afd65397da3df69e2de42dabf35c34d4e176136abd | c1ccc2[nH]ccc2c1 | F-C(-F)(-F)-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7](-[C;D1;H3:8]):[c;H0;D3;+0:9](-O-S(-O)(=O)=O):[c:10]:2:1.[C;D1;H3:11]-[#8:12]-[C:13](=[O;D1;H0:14])-[C:15]=[CH2;D1;+0:16]>>[C;D1;H3:8]-[c:7]1:[#7;a:6]:[c:5]2:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[CH;D2;+0:16]=[C:15]-[C:13](=[O;D1;H0:14])-[#8:12]-[C;D1;H3:1... | null | [] | 95 | CELSIUS | 2 | DAY | To a solution 2-methyl-4-trifluoromethylsulfoxyindole (3.2 g; prepared in Reference Example 2) in N,N-dimethylformamide (50 ml) was added acrylic acid methyl ester (2.24 ml), diisopropylethylamine (5.9 ml) and dichlorobis(triphenylphosphine)palladium(II) (238 mg), and the mixture was stirred at 95° C. for 2 days. To th... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Sulfate.Vinyl | null | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | HF | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.CN(C=O)C.C(C)(=O)OCC | 95 | 48 | C=CC(=O)OC.Cc1[nH]c2cccc(C(F)(F)F)c2c1OS(=O)(=O)O>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.CN(C=O)C.C(C)(=O)OCC>COC(=O)C=Cc1cccc2[nH]c(C)cc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fbbdc2ab01dd4be3a3c7f7fcee3fd11e | CCCCOc1ccc(C(=O)n2c(C)cc3c(C=CC(=O)O)cccc32)cc1>>CCCCOc1ccc(C(=O)n2c(C)cc3c(CCC(=O)O)cccc32)cc1 | C(CCC)OC1=CC=C(C(=O)N2C(=CC3=C(C=CC=C23)C=CC(=O)O)C)C=C1.[H][H]>>C(CCC)OC1=CC=C(C(=O)N2C(=CC3=C(C=CC=C23)CCC(=O)O)C)C=C1 | [CH3:1][CH2:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]([C:10](=[O:11])[n:12]2[c:13]([CH3:14])[cH:15][c:16]3[c:17]([CH:18]=[CH:19][C:20](=[O:21])[OH:22])[cH:23][cH:24][cH:25][c:26]23)[cH:27][cH:28]1>>[CH3:1][CH2:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]([C:10](=[O:11])[n:12]2[c:13]([CH3:14])[cH:15][c:16]3[c:17]([CH... | CCCCOc1ccc(C(=O)n2c(C)cc3c(C=CC(=O)O)cccc32)cc1 | CCCCOc1ccc(C(=O)n2c(C)cc3c(CCC(=O)O)cccc32)cc1 | null | [Pd] | CO.C(C)(=O)OCC | Reduction | Hydrogenation (double to single) | 0bc3968b35f0839c230afb4215314da278abd4e1f10e42ec3012c5512de49ea5 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | O=C(c1ccccc1)n1ccc2ccccc21 | [#7;a:1]:[c:2]:[c:3]:[c:4](-[CH;D2;+0:5]=[CH;D2;+0:6]-[C:7](=[O;D1;H0:8])-[O;D1;H1:9]):[c:10]>>[#7;a:1]:[c:2]:[c:3]:[c:4](-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[C:7](=[O;D1;H0:8])-[O;D1;H1:9]):[c:10] | 8.3 | [{"value": 8.3, "product": "C(CCC)OC1=CC=C(C(=O)N2C(=CC3=C(C=CC=C23)CCC(=O)O)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 3-(1-(4-butoxybenzoyl)-2-methylindol-4-yl)acrylic acid (300 mg; prepared in Example 4) in methanol-ethyl acetate (5 ml+5 ml) was added palladium on activated carbon (100 mg) at room temperature. The inside of the vessel was replaced with hydrogen and the mixture was stirred at room temperature for 2 ho... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.c1cc2ccccc2[nH]1 | null | [Pd].CO.C(C)(=O)OCC | null | 2 | CCCCOc1ccc(C(=O)n2c(C)cc3c(C=CC(=O)O)cccc32)cc1>[Pd].CO.C(C)(=O)OCC>CCCCOc1ccc(C(=O)n2c(C)cc3c(CCC(=O)O)cccc32)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a84bb63544524f4eb4575caeb8371555 | CC(=O)Oc1ccc(C(=O)O)cc1.O=C(Cl)C(=O)Cl>>CC(=O)Oc1ccc(C(=O)Cl)cc1 | C(C)(=O)OC1=CC=C(C(=O)O)C=C1.C(C(=O)Cl)(=O)Cl>>C(C)(=O)OC1=CC=C(C(=O)Cl)C=C1 | O[C:9]([c:8]1[cH:7][cH:6][c:5]([O:4][C:2]([CH3:1])=[O:3])[cH:13][cH:12]1)=[O:10].O=C(Cl)C(=O)[Cl:11]>>[CH3:1][C:2](=[O:3])[O:4][c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[Cl:11])[cH:12][cH:13]1 | CC(=O)Oc1ccc(C(=O)O)cc1.O=C(Cl)C(=O)Cl | CC(=O)Oc1ccc(C(=O)Cl)cc1 | null | null | null | Functional Group Interconversion | Alcohol to chloride_Other | 013cec2edeb273a7a148f349d36a52d99ff4e7bcf8eed78085df830088e387ac | aedb1f68dc5b7eb0583043e1125b741382b17974140a2f46554f0110e2ddc884 | c1ccccc1 | Cl-C(=O)-C(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]>>[Cl;H0;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | 30 | MINUTE | A mixture of 4-acetoxybenzoic acid (516 mg) and oxalyl chloride (0.5 ml) was stirred for 30 minutes. The mixture was concentrated under reduced pressure to give 4-acetoxybenzoyl chloride.
Conditions: See reaction.notes.procedure_details.
Workup: The mixture was concentrated under reduced pressure | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Carboxylic acid | Acyl halide | null | null | c1ccccc1 | HCl | null | null | 0.5 | CC(=O)Oc1ccc(C(=O)O)cc1.O=C(Cl)C(=O)Cl>>CC(=O)Oc1ccc(C(=O)Cl)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f7ee27120d3e45df9a00b6188ab0a4c8 | COC(=O)c1ccc(N)cc1.II>>COC(=O)c1ccc(N)c(I)c1 | NC1=CC=C(C(=O)OC)C=C1.II>>NC1=C(C=C(C(=O)OC)C=C1)I | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH2:9])[cH:10][cH:12]1.I[I:11]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH2:9])[c:10]([I:11])[cH:12]1 | COC(=O)c1ccc(N)cc1.II | COC(=O)c1ccc(N)c(I)c1 | null | S(=O)(=O)([O-])[O-].[Ag+2] | C(C)O | Functional Group Interconversion | OtherReaction | f6effe61353895b318215d8bd9b6bb1105cafbf7be8c217d748df587260b32c3 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccccc1 | I-[I;H0;D1;+0:1].[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]:[c:6]:[cH;D2;+0:7]:[c:8](-[N;D1;H2:9]):[c:10]>>[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]:[c:6]:[c;H0;D3;+0:7](-[I;H0;D1;+0:1]):[c:8](-[N;D1;H2:9]):[c:10] | null | [] | null | null | 18 | HOUR | Methyl 4-aminobenzoate (30.23 g, 200 mmol) was added to a mixture of iodine (60.91 g, 240 mmol) and silver sulfate (81.07 g, 260 mmol) in 1 L of ethanol at room temperature. The mixture was stirred at room temperature for 18 hours, filtered over Celite and the filtrate was evaporated to dryness under reduced pressure. ... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | HI | S(=O)(=O)([O-])[O-].[Ag+2].C(C)O | null | 18 | COC(=O)c1ccc(N)cc1.II>S(=O)(=O)([O-])[O-].[Ag+2].C(C)O>COC(=O)c1ccc(N)c(I)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2a913d18f5f04d3f8b60c7d5ab1a93c6 | COC(=O)c1ccc(N)c(I)c1.O=C1CCCC1>>COC(=O)c1ccc(NC2CCCC2)c(I)c1 | C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+].NC1=C(C=C(C(=O)OC)C=C1)I.C1(CCCC1)=O.S(=O)(=O)([O-])[O-].[Na+].[Na+].C([O-])(O)=O.[Na+]>>C1(CCCC1)NC1=C(C=C(C(=O)OC)C=C1)I | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH2:9])[c:15]([I:16])[cH:17]1.O=[C:10]1[CH2:11][CH2:12][CH2:13][CH2:14]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH:9][CH:10]2[CH2:11][CH2:12][CH2:13][CH2:14]2)[c:15]([I:16])[cH:17]1 | COC(=O)c1ccc(N)c(I)c1.O=C1CCCC1 | COC(=O)c1ccc(NC2CCCC2)c(I)c1 | null | null | C(C)(=O)O | Heteroatom Alkylation and Arylation | Reductive amination with ketone | b85679fed5f5625b57908374666b40667904d1ae7fb913f5564f84f7e4e3c6f0 | 07faf85ffe990e88a1de7fd04a339bf226f78d8bfae9712ea59eebd76bb54b9f | c1ccc(NC2CCCC2)cc1 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1.[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[CH;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1):[c:9] | null | [] | null | null | 2 | HOUR | A mixture of methyl 4-amino-3-iodobenzoate from above (27.69 g, 100 mmol), cyclopentanone (52.8 mL, 600 mmol), and anhydrous sodium sulfate (1000 g, 142 mmol) in 500 mL of glacial acetic acid was stirred for two hours. Solid sodium triacetoxyborohydride (76.92, 345 mmol) was added in portions and stirred for 16 hrs at ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Secondary amine | C1CCCC1 | C1CCCC1 | c1ccccc1.C1CCCC1 | Other | C(C)(=O)O | null | 2 | COC(=O)c1ccc(N)c(I)c1.O=C1CCCC1>C(C)(=O)O>COC(=O)c1ccc(NC2CCCC2)c(I)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7c499243f8554ab3be13ddeac722ac3c | CC#C[Si](C)(C)C.COC(=O)c1ccc(NC2CCCC2)c(I)c1>>COC(=O)c1ccc2c(c1)c(C)c([Si](C)(C)C)n2C1CCCC1 | C1(CCCC1)NC1=C(C=C(C(=O)OC)C=C1)I.[Cl-].[Li+].C(C)(=O)[O-].[K+].C[Si](C#CC)(C)C.[Cl-].[NH4+]>>C1(CCCC1)N1C(=C(C2=CC(=CC=C12)C(=O)OC)C)[Si](C)(C)C | [C:11]([CH3:12])#[C:13][Si:14]([CH3:15])([CH3:16])[CH3:17].I[c:9]1[c:8]([NH:18][CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23]2)[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:10]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[c:11]([CH3:12])[c:13]([Si:14]([CH3:15])([CH3:16])[CH3:17])[n:18]2[CH:19]1[CH2:20... | CC#C[Si](C)(C)C.COC(=O)c1ccc(NC2CCCC2)c(I)c1 | COC(=O)c1ccc2c(c1)c(C)c([Si](C)(C)C)n2C1CCCC1 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | 23a0c3325817e6ea7e503e441cbfee1ddeb0326d991729841a65c39c721eb0a5 | ed1625e7fdb41ec70afd6cf2c917cd7f0882691c4622be0b2f9f6302b6ca81b8 | c1ccc2c(c1)ccn2C1CCCC1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4](-[#8:5])=[O;D1;H0:6]):[c:7](-[NH;D2;+0:8]-[C:9](-[C:10])-[C:11]):[c:12].[C;D1;H3:13]-[C;H0;D2;+0:14]#[C;H0;D2;+0:15]-[#14:16](-[C;D1;H3:17])(-[C;D1;H3:18])-[C;D1;H3:19]>>[#8:5]-[C:4](=[O;D1;H0:6])-[c:3]:[c:2]:[c;H0;D3;+0:1]1:[c:7](:[c:12]):[n;H0;D3;+0:8](-[C:9](-[C:10])-[C:11]):[c;H0... | 75 | [{"value": 75.0, "product": "C1(CCCC1)N1C(=C(C2=CC(=CC=C12)C(=O)OC)C)[Si](C)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | A mixture of methyl 4-(N-cyclopentylamino)-3-iodobenzoate from above (22.42 g, 65 mmol), palladium acetate (738 mg, 3.28 mmol), lithium chloride (2.757 g, 65 mmol), potassium acetate (12.757 g, 92.30 mmol), and 1-trimethylsilyl-1-propyne (28.70 mL, 192.56 mmol) in 390 mL of DMF was heated at 100° C. for 6 hours. The mi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine.Alkyne | null | c1ccccc1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.C1CCCC1 | HI | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].CN(C)C=O | 100 | null | CC#C[Si](C)(C)C.COC(=O)c1ccc(NC2CCCC2)c(I)c1>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].CN(C)C=O>COC(=O)c1ccc2c(c1)c(C)c([Si](C)(C)C)n2C1CCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-94e6a89524ad4bca9996f48f9741aa00 | Brc1cc2ccccc2[nH]1.Brc1ccccn1.C1CCOC1.COB(OC)OC>>COC(=O)c1ccc2c(c1)c(C)c(-c1ccccn1)n2C1CCCC1 | C([O-])([O-])=O.[K+].[K+].C1(=CC=C(C=C1)P)C.BrC1=NC=CC=C1.COB(OC)OC.C1CCOC1.BrC=1NC2=CC=CC=C2C1.C1CCOC1>>C1(CCCC1)N1C(=C(C2=CC(=CC=C12)C(=O)OC)C)C1=NC=CC=C1 | Br[c:13]1[cH:11][c:9]2[c:8]([cH:7][cH:6][cH:5][cH:10]2)[nH:20]1.Br[c:14]1[cH:15][cH:16][cH:17][cH:18][n:19]1.O1[CH2:22][CH2:23][CH2:24][CH2:25]1.COB(OC)O[CH3:1]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[c:11]([CH3:12])[c:13](-[c:14]1[cH:15][cH:16][cH:17][cH:18][n:19]1)[n:20]2[CH:21]1[CH2:22][CH2... | Brc1cc2ccccc2[nH]1.Brc1ccccn1.C1CCOC1.COB(OC)OC | COC(=O)c1ccc2c(c1)c(C)c(-c1ccccn1)n2C1CCCC1 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | CO.O.CC(C)(C)OC | Acylation | OtherReaction | 3c05d7047544c68709f686282f676681670fb0436de2315fd0f1b935dc608610 | 0d9903258b8959f074d966c5210a26503a5548b0e28b6063083c10c14de56d95 | c1ccc(-c2cc3ccccc3n2C2CCCC2)nc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].Br-[c;H0;D3;+0:6]1:[cH;D2;+0:7]:[c:8]2:[c:9]:[cH;D2;+0:10]:[c:11]:[c:12]:[c:13]:2:[nH;D2;+0:14]:1.C-O-B(-O-C)-O-[CH3;D1;+0:15].O1-[CH2;D2;+0:16]-[C:17]-[C:18]-[CH2;D2;+0:19]-1>>[C;D1;H3:20]-[c;H0;D3;+0:7]1:[c:8]2:[c:9]:[c;H0;D3;+0:10](-[C:21](=[O;D1;H0:22])-[#8:23]-[CH3;D1... | null | [] | -78 | CELSIUS | 30 | MINUTE | The 2-bromoindole from above (1.53 g, 4.55 mmol, 1.0 equiv.) was dissolved in anhydrous THF (20 mL) and the solution was cooled to −78° C. under an argon atmosphere. N-BuLi (solution in hexane, 4.78 mmol, 1.05 equiv.) was added dropwise and the mixture was stirred 30 min in the cold. Trimethylborate (0.62 mL, 5.46 mmol... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Ether | Ester | c1ccc2[nH]ccc2c1.c1ccncc1.C1CCOC1 | c1ccc2[nH]ccc2c1.c1ccncc1.C1CCCC1 | c1ccc2[nH]ccc2c1.c1ccncc1.C1CCCC1 | HBr.B | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].CO.O.CC(C)(C)OC | -78 | 0.5 | Brc1cc2ccccc2[nH]1.Brc1ccccn1.C1CCOC1.COB(OC)OC>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].CO.O.CC(C)(C)OC>COC(=O)c1ccc2c(c1)c(C)c(-c1ccccn1)n2C1CCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ad431575cf5e4313ab0e837e19d4f850 | NC1CC1.N[C@@H](CC(=O)N1CCC[C@H]1C(=O)NCc1cc(Cl)ccc1OCC(=O)O)Cc1ccccc1>>N[C@@H](CC(=O)N1CCC[C@H]1C(=O)NCc1cc(Cl)ccc1OCC(=O)NC1CC1)Cc1ccccc1 | C(N)(OC(C)(C)C)=O.N[C@@H](CC(=O)N1[C@H](C(=O)NCC2=C(OCC(=O)O)C=CC(=C2)Cl)CCC1)CC1=CC=CC=C1.C1(CC1)N>>N[C@@H](CC(=O)N1[C@H](C(=O)NCC2=C(C=CC(=C2)Cl)OCC(=O)NC2CC2)CCC1)CC1=CC=CC=C1 | [NH2:26][CH:27]1[CH2:28][CH2:29]1.O[C:24]([CH2:23][O:22][c:21]1[c:15]([CH2:14][NH:13][C:11]([C@H:10]2[N:6]([C:4]([CH2:3][C@H:2]([NH2:1])[CH2:30][c:31]3[cH:32][cH:33][cH:34][cH:35][cH:36]3)=[O:5])[CH2:7][CH2:8][CH2:9]2)=[O:12])[cH:16][c:17]([Cl:18])[cH:19][cH:20]1)=[O:25]>>[NH2:1][C@@H:2]([CH2:3][C:4](=[O:5])[N:6]1[CH2:... | NC1CC1.N[C@@H](CC(=O)N1CCC[C@H]1C(=O)NCc1cc(Cl)ccc1OCC(=O)O)Cc1ccccc1 | N[C@@H](CC(=O)N1CCC[C@H]1C(=O)NCc1cc(Cl)ccc1OCC(=O)NC1CC1)Cc1ccccc1 | null | null | CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(COc1ccccc1CNC(=O)[C@@H]1CCCN1C(=O)CCCc1ccccc1)NC1CC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#8:4].[NH2;D1;+0:5]-[C:6]1-[C:7]-[C:8]-1>>[#8:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[C:6]1-[C:7]-[C:8]-1 | null | [] | null | null | null | null | A solution of 46 mg (0.08 mmol) of the tert butyl carbamate of {2-[({1-[(3R)-3-amino-4-phenylbutanoyl]-L-prolyl}amino)methyl]-4-chlorophenoxyacetic acid and 0.0055 mL (0.096 mmol) of cyclopropylamine in DMF were coupled and deprotected as described for Example 1, Step C and D to give 25 mg of the title compound. 1H NMR... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1CC[NH]C1.c1ccccc1.C1CC1.c1ccccc1 | HO- | CN(C)C=O | null | null | NC1CC1.N[C@@H](CC(=O)N1CCC[C@H]1C(=O)NCc1cc(Cl)ccc1OCC(=O)O)Cc1ccccc1>CN(C)C=O>N[C@@H](CC(=O)N1CCC[C@H]1C(=O)NCc1cc(Cl)ccc1OCC(=O)NC1CC1)Cc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b307f8696e4749439cc0b1517f8db6d3 | N[C@@H](CC(=O)N1CCC[C@H]1C(=O)NCc1cc(Cl)ccc1OCC(=O)NC1CC1)Cc1ccccc1>>N[C@@H](CC(=O)N1CCC[C@H]1C(=O)NCc1ccccc1OCC(=O)NC1CC1)Cc1ccccc1 | [H][H].N[C@@H](CC(=O)N1[C@H](C(=O)NCC2=C(C=CC(=C2)Cl)OCC(=O)NC2CC2)CCC1)CC1=CC=CC=C1>>N[C@@H](CC(=O)N1[C@H](C(=O)NCC2=C(C=CC=C2)OCC(=O)NC2CC2)CCC1)CC1=CC=CC=C1 | Cl[c:17]1[cH:16][c:15]([CH2:14][NH:13][C:11]([C@H:10]2[N:6]([C:4]([CH2:3][C@H:2]([NH2:1])[CH2:29][c:30]3[cH:31][cH:32][cH:33][cH:34][cH:35]3)=[O:5])[CH2:7][CH2:8][CH2:9]2)=[O:12])[c:20]([O:21][CH2:22][C:23](=[O:24])[NH:25][CH:26]2[CH2:27][CH2:28]2)[cH:19][cH:18]1>>[NH2:1][C@@H:2]([CH2:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8... | N[C@@H](CC(=O)N1CCC[C@H]1C(=O)NCc1cc(Cl)ccc1OCC(=O)NC1CC1)Cc1ccccc1 | N[C@@H](CC(=O)N1CCC[C@H]1C(=O)NCc1ccccc1OCC(=O)NC1CC1)Cc1ccccc1 | null | [OH-].[OH-].[Pd+2] | CO | Functional Group Interconversion | Aromatic dehalogenation | b66818d3926a4463fb8e1c3d4a89e94e47b4d46960d4bdb7bcfbeeec427cfd4e | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | O=C(COc1ccccc1CNC(=O)[C@@H]1CCCN1C(=O)CCCc1ccccc1)NC1CC1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]>>[c:3]:[c:2]:[cH;D2;+0:1]:[c:4]:[c:5] | 71.5 | [{"value": 71.5, "product": "N[C@@H](CC(=O)N1[C@H](C(=O)NCC2=C(C=CC=C2)OCC(=O)NC2CC2)CCC1)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Palladium hydroxide on activated charcoal (˜50 mg) was added to a solution of 15 mg of 1-[(3R)-3-amino-4-phenylbutanoyl]-N-{5-chloro-2-[2-(cyclopropylamino)-2-oxoethoxy]benzyl }-L-prolinamide in 1 mL methanol and the mixture was stirred under a balloon of hydrogen for 6 h. The reaction was diluted with methanol, filter... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccccc1 | c1ccccc1 | C1CC[NH]C1.c1ccccc1.C1CC1.c1ccccc1 | Other | [OH-].[OH-].[Pd+2].CO | null | null | N[C@@H](CC(=O)N1CCC[C@H]1C(=O)NCc1cc(Cl)ccc1OCC(=O)NC1CC1)Cc1ccccc1>[OH-].[OH-].[Pd+2].CO>N[C@@H](CC(=O)N1CCC[C@H]1C(=O)NCc1ccccc1OCC(=O)NC1CC1)Cc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f0c8411110a14024be0381e63896f360 | NC(=O)c1ccsc1N.O=C=NC(=O)C(Cl)(Cl)Cl>>NC(=O)Nc1sccc1C(N)=O | NC=1SC=CC1C(=O)N.ClC(C(=O)N=C=O)(Cl)Cl.N>>NC(=O)NC=1SC=CC1C(=O)N | [NH2:4][c:5]1[s:6][cH:7][cH:8][c:9]1[C:10]([NH2:11])=[O:12].O=C(C(Cl)(Cl)Cl)[N:1]=[C:2]=[O:3]>>[NH2:1][C:2](=[O:3])[NH:4][c:5]1[s:6][cH:7][cH:8][c:9]1[C:10]([NH2:11])=[O:12] | NC(=O)c1ccsc1N.O=C=NC(=O)C(Cl)(Cl)Cl | NC(=O)Nc1sccc1C(N)=O | null | null | CO.C(C)#N | Acylation | OtherReaction | 13049a4aa8e5bdfadb87752f84471e3324b9668d4dd6524fa5e40bd91c8996d5 | 21f5b10ff9a286ca62666d6d70da1376e15ff88ed743ce59beae5e1025149ef1 | c1ccsc1 | Cl-C(-Cl)(-Cl)-C(=O)-[N;H0;D2;+0:1]=[C;H0;D2;+0:2]=[O;D1;H0:3].[N;D1;H2:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[NH2;D1;+0:9]):[#16;a:10]:[c:11]>>[N;D1;H2:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[NH;D2;+0:9]-[C;H0;D3;+0:2](-[NH2;D1;+0:1])=[O;D1;H0:3]):[#16;a:10]:[c:11] | null | [] | null | null | 10 | MINUTE | 2-Amino-3-thiophencarboxamide (0.44 g) was suspended in acetonitrile (25 ml) and trichloroacetylisocyanate (0.2 ml) added dropwise with stirring over 10 minutes. Stirring was continued for a further 3 h at room temperature and then a solution of ammonia in methanol (10 ml of a 2M solution) was added and stirring was co... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Isocyanate.Primary amine | Urea | null | null | c1ccsc1 | Other | CO.C(C)#N | null | 0.166667 | NC(=O)c1ccsc1N.O=C=NC(=O)C(Cl)(Cl)Cl>CO.C(C)#N>NC(=O)Nc1sccc1C(N)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4d1da4d0918448bfb632e3f26c195eee | BrBr.NC(=O)Nc1sccc1C(N)=O>>NC(=O)Nc1sc(Br)cc1C(N)=O | NC(=O)NC=1SC=CC1C(=O)N.BrBr.O>>NC(=O)NC=1SC(=CC1C(=O)N)Br | Br[Br:8].[NH2:1][C:2](=[O:3])[NH:4][c:5]1[s:6][cH:7][cH:9][c:10]1[C:11]([NH2:12])=[O:13]>>[NH2:1][C:2](=[O:3])[NH:4][c:5]1[s:6][c:7]([Br:8])[cH:9][c:10]1[C:11]([NH2:12])=[O:13] | BrBr.NC(=O)Nc1sccc1C(N)=O | NC(=O)Nc1sc(Br)cc1C(N)=O | null | null | C(C)(=O)O | Functional Group Interconversion | Bromination | 4c699ee9b1951af9f1cb735a87e324fa1208b45d074146a138e8c7ebdaaf12cc | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccsc1 | Br-[Br;H0;D1;+0:1].[N;D1;H2:2]-[C:3](=[O;D1;H0:4])-[c:5]1:[c:6]:[#16;a:7]:[cH;D2;+0:8]:[c:9]:1>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:8]1:[#16;a:7]:[c:6]:[c:5](-[C:3](-[N;D1;H2:2])=[O;D1;H0:4]):[c:9]:1 | null | [] | null | null | 90 | MINUTE | 2-[(Aminocarbonyl)amino]-3-thiophenecarboxamide (1.0 g) was dissolved in acetic acid (20 ml) and a solution of bromine (0.35 ml) in acetic acid (5 ml) was added over 5 minutes with rapid stirring. The mixture was stirred for 90 minutes and then added to water (50 ml). The product was filtered off and washed with water ... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccsc1 | c1ccsc1 | c1ccsc1 | HBr | C(C)(=O)O | null | 1.5 | BrBr.NC(=O)Nc1sccc1C(N)=O>C(C)(=O)O>NC(=O)Nc1sc(Br)cc1C(N)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0e662e7479ec46efaff48fad19e2d336 | Cc1c(-c2ccc3c(c2)OCCO3)sc(N)c1C(N)=O.O=C=NC(=O)C(Cl)(Cl)Cl>>Cc1c(-c2ccc3c(c2)OCCO3)sc(NC(N)=O)c1C(N)=O | N.ClC(C(=O)N=C=O)(Cl)Cl.NC=1SC(=C(C1C(=O)N)C)C1=CC2=C(OCCO2)C=C1>>NC(=O)NC=1SC(=C(C1C(=O)N)C)C1=CC2=C(OCCO2)C=C1 | [CH3:1][c:2]1[c:3](-[c:4]2[cH:5][cH:6][c:7]3[c:8]([cH:9]2)[O:10][CH2:11][CH2:12][O:13]3)[s:14][c:15]([NH2:16])[c:20]1[C:21]([NH2:22])=[O:23].O=C(C(Cl)(Cl)Cl)[N:18]=[C:17]=[O:19]>>[CH3:1][c:2]1[c:3](-[c:4]2[cH:5][cH:6][c:7]3[c:8]([cH:9]2)[O:10][CH2:11][CH2:12][O:13]3)[s:14][c:15]([NH:16][C:17]([NH2:18])=[O:19])[c:20]1[C... | Cc1c(-c2ccc3c(c2)OCCO3)sc(N)c1C(N)=O.O=C=NC(=O)C(Cl)(Cl)Cl | Cc1c(-c2ccc3c(c2)OCCO3)sc(NC(N)=O)c1C(N)=O | null | null | CO.O1CCCC1 | Acylation | OtherReaction | 13049a4aa8e5bdfadb87752f84471e3324b9668d4dd6524fa5e40bd91c8996d5 | 21f5b10ff9a286ca62666d6d70da1376e15ff88ed743ce59beae5e1025149ef1 | c1csc(-c2ccc3c(c2)OCCO3)c1 | Cl-C(-Cl)(-Cl)-C(=O)-[N;H0;D2;+0:1]=[C;H0;D2;+0:2]=[O;D1;H0:3].[N;D1;H2:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[NH2;D1;+0:9]):[#16;a:10]:[c:11]>>[N;D1;H2:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[NH;D2;+0:9]-[C;H0;D3;+0:2](-[NH2;D1;+0:1])=[O;D1;H0:3]):[#16;a:10]:[c:11] | null | [] | 0 | CELSIUS | 30 | MINUTE | 2-Amino-4-methyl-5-(1,4-benzodioxan-6-yl)-3-thiophencarboxamide (0.44 g) was dissolved in tetrahydrofuran (10 ml), cooled to 0° C. and trichloroacetylisocyanate (0.11 ml) added dropwise with stirring. Stirring was continued for a further 30 minutes at room temperature and then a solution of ammonia in methanol (8 ml of... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Isocyanate.Primary amine | Urea | null | null | c1ccsc1.c1ccc2c(c1)OCCO2 | Other | CO.O1CCCC1 | 0 | 0.5 | Cc1c(-c2ccc3c(c2)OCCO3)sc(N)c1C(N)=O.O=C=NC(=O)C(Cl)(Cl)Cl>CO.O1CCCC1>Cc1c(-c2ccc3c(c2)OCCO3)sc(NC(N)=O)c1C(N)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0290ac04ad0e445e81e62a6c3df508c9 | CC(C)(C)OC(=O)Nc1cc(Br)sc1C(=O)O.N>>CC(C)(C)OC(=O)Nc1cc(Br)sc1C(N)=O | N.OC1=CC=CC=2NN=NC21.Cl.CN(CCCN=C=NCC)C.BrC1=CC(=C(S1)C(=O)O)NC(=O)OC(C)(C)C>>BrC1=CC(=C(S1)C(=O)N)NC(=O)OC(C)(C)C | O[C:15]([c:14]1[c:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[cH:10][c:11]([Br:12])[s:13]1)=[O:17].[NH3:16]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:9]1[cH:10][c:11]([Br:12])[s:13][c:14]1[C:15]([NH2:16])=[O:17] | CC(C)(C)OC(=O)Nc1cc(Br)sc1C(=O)O.N | CC(C)(C)OC(=O)Nc1cc(Br)sc1C(N)=O | null | null | C(C)#N | Acylation | Carboxylic acid to amide conversion | 1283aef55d7ee699f097a8e5267689198c76ba671644401547f902657820236d | cb0a71c3fb37a76e96fbd81aae6f95a28398a03d1ad2c8e877085e735efb98f1 | c1ccsc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#16;a:5]:[c:6].[NH3;D0;+0:7]>>[NH2;D1;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#16;a:5]:[c:6] | null | [] | null | null | 10 | MINUTE | 5-Bromo-3-[(t-butyloxycarbonyl)amino]thiophene-2-carboxylic acid (0.80 g) was stirred in acetonitrile (80 ml). Hydroxybenztriazole (1.41 g) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.62 g) were added and stirring continued at room temperature for 10 minutes. Concentrated aqueous ammonia solution... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary amide | null | null | c1ccsc1 | HO- | C(C)#N | null | 0.166667 | CC(C)(C)OC(=O)Nc1cc(Br)sc1C(=O)O.N>C(C)#N>CC(C)(C)OC(=O)Nc1cc(Br)sc1C(N)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a3b9c32ae59b4f06a3e70b55003233e4 | CC(C)(C)OC(=O)Nc1cc(Br)sc1C(N)=O>>NC(=O)c1sc(Br)cc1N | BrC1=CC(=C(S1)C(=O)N)NC(=O)OC(C)(C)C.FC(C(=O)O)(F)F.C(O)([O-])=O.[Na+]>>NC1=C(SC(=C1)Br)C(=O)N | CC(C)(C)OC(=O)[NH:10][c:9]1[c:4]([C:2]([NH2:1])=[O:3])[s:5][c:6]([Br:7])[cH:8]1>>[NH2:1][C:2](=[O:3])[c:4]1[s:5][c:6]([Br:7])[cH:8][c:9]1[NH2:10] | CC(C)(C)OC(=O)Nc1cc(Br)sc1C(N)=O | NC(=O)c1sc(Br)cc1N | null | null | ClCCl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccsc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#16;a:5]:[c:6]:1-[C:7](-[N;D1;H2:8])=[O;D1;H0:9]>>[N;D1;H2:8]-[C:7](=[O;D1;H0:9])-[c:6]1:[#16;a:5]:[c:4]:[c:3]:[c:2]:1-[NH2;D1;+0:1] | 97.7 | [{"value": 97.7, "product": "NC1=C(SC(=C1)Br)C(=O)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 5-Bromo-3-(t-butyloxycarbonyl)aminothiophene-2-carboxamide (0.76 g) was stirred in dichloromethane (30 ml). Trifluoroacetic acid (51 ml) was added, the solution was stirred at room temperature for 1 h, poured into saturated aqueous sodium hydrogen carbonate solution (200 ml) and extracted with dichloromethane (3×100 ml... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccsc1 | HO- | ClCCl | null | 1 | CC(C)(C)OC(=O)Nc1cc(Br)sc1C(N)=O>ClCCl>NC(=O)c1sc(Br)cc1N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-798a65328c5e4ea19223cb360c86736d | NC(=O)Nc1cc(Br)sc1C(N)=O.OB(O)c1csc2ccccc12>>NC(=O)Nc1cc(-c2csc3ccccc23)sc1C(N)=O | NC(=O)NC1=C(SC(=C1)Br)C(=O)N.S1C=C(C2=C1C=CC=C2)B(O)O>>NC(=O)NC1=C(SC(=C1)C1=CSC2=C1C=CC=C2)C(=O)N | Br[c:7]1[cH:6][c:5]([NH:4][C:2]([NH2:1])=[O:3])[c:18]([C:19]([NH2:20])=[O:21])[s:17]1.OB(O)[c:8]1[cH:9][s:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]12>>[NH2:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7](-[c:8]2[cH:9][s:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]23)[s:17][c:18]1[C:19]([NH2:20])=[O:21] | NC(=O)Nc1cc(Br)sc1C(N)=O.OB(O)c1csc2ccccc12 | NC(=O)Nc1cc(-c2csc3ccccc23)sc1C(N)=O | null | null | COCCOC | C-C Coupling | Suzuki coupling with boronic acids | 9afab3685eed4a926cff56f3cd0d2eb48abffd401e4ed0c15bf27573a5ca78bf | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1csc(-c2csc3ccccc23)c1 | Br-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3](-[C:4](-[N;D1;H2:5])=[O;D1;H0:6]):[c:7]:[c:8]:1.O-B(-O)-[c;H0;D3;+0:9]1:[c:10]:[#16;a:11]:[c:12](:[c:13]):[c:14]:1:[c:15]>>[N;D1;H2:5]-[C:4](=[O;D1;H0:6])-[c:3]1:[#16;a:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:9]2:[c:10]:[#16;a:11]:[c:12](:[c:13]):[c:14]:2:[c:15]):[c:8]:[c:7]:1 | null | [] | null | null | 4.5 | HOUR | 3-[(Aminocarbonyl)amino-5-bromothiophene-2-carboxamide (0.222 g) and 1-benzothien-3-ylboronic acid (0.449 g) were sonicated in 1,2-dimethoxyethane (15 ml) and saturated aqueous sodium hydrogen carbonate solution (3.5 ml) and purged with argon. Tetrakis(triphenylphosphine)-palladium (95 mg) was added and the mixture was... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccsc1.c1ccc2sccc2c1 | c1ccsc1.c1ccc2sccc2c1 | c1ccsc1.c1ccc2sccc2c1 | HBr.B | COCCOC | null | 4.5 | NC(=O)Nc1cc(Br)sc1C(N)=O.OB(O)c1csc2ccccc12>COCCOC>NC(=O)Nc1cc(-c2csc3ccccc23)sc1C(N)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2afdbf5b452c4473aa1f7b3a5c5a3a04 | ClCCN1CCOCC1.Oc1cccc2sccc12>>c1cc(OCCC2CNCCO2)c2ccsc2c1 | O.Cl.ClCCN1CCOCC1.S1C=CC=2C1=CC=CC2O.C([O-])([O-])=O.[K+].[K+].CN(C=O)C>>S1C=CC2=C1C=CC=C2OCCC2CNCCO2 | Cl[CH2:5][CH2:6][N:9]1[CH2:8][CH2:7][O:12][CH2:11][CH2:10]1.[cH:1]1[cH:2][c:3]([OH:4])[c:13]2[cH:14][cH:15][s:16][c:17]2[cH:18]1>>[cH:1]1[cH:2][c:3]([O:4][CH2:5][CH2:6][CH:7]2[CH2:8][NH:9][CH2:10][CH2:11][O:12]2)[c:13]2[cH:14][cH:15][s:16][c:17]2[cH:18]1 | ClCCN1CCOCC1.Oc1cccc2sccc12 | c1cc(OCCC2CNCCO2)c2ccsc2c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | c2d741cf367c42862d7ad27ecf7955b3c7888392d78d008c055a97ff6fd6520a | e746f748a671a5fdb6116cafd253e61a570ee801722200198985f49076d757dc | c1cc(OCCC2CNCCO2)c2ccsc2c1 | Cl-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[N;H0;D3;+0:3]1-[C:4]-[C:5]-[#8:6]-[CH2;D2;+0:7]-[C:8]-1.[#16;a:9]:[c:10]:[c:11]:[c:12](-[OH;D1;+0:13]):[c:14]>>[#16;a:9]:[c:10]:[c:11]:[c:12](-[O;H0;D2;+0:13]-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[CH;D3;+0:7]1-[#8:6]-[C:5]-[C:4]-[NH;D2;+0:3]-[C:8]-1):[c:14] | null | [] | 80 | CELSIUS | 6 | HOUR | 4-(2-Chloroethyl)morpholine hydrochloride (0.74 g), 1-benzothiophene-4-ol (0.5 g) and potassium carbonate (1.1 g) in dimethylformamide (15 ml) were heated and stirred at 80° C. for 6 h. After cooling, the mixture was poured into water and extracted twice with ethyl acetate. The combined solvent phase was washed twice w... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Aromatic alcohol.Tertiary amine | Ether.Ether.Secondary amine | C1COCC[NH]1 | C1COCCN1 | C1COCCN1.c1ccc2sccc2c1 | HCl | null | 80 | 6 | ClCCN1CCOCC1.Oc1cccc2sccc12>>c1cc(OCCC2CNCCO2)c2ccsc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-760b60ae9f0d4a8cb3a157644a6f1fab | Cc1ccc(S(=O)(=O)Cl)cc1.NCCc1cccc(Br)c1>>Cc1ccc(S(=O)(=O)C(CN)c2cccc(Br)c2)cc1 | C(C)N(CC)CC.Cl.BrC=1C=C(C=CC1)CCN.CC1=CC=C(C=C1)S(=O)(=O)Cl>>BrC=1C=C(C=CC1)C(CN)S(=O)(=O)C1=CC=C(C=C1)C | Cl[S:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:20][cH:19]1)(=[O:7])=[O:8].[CH2:9]([CH2:10][NH2:11])[c:12]1[cH:13][cH:14][cH:15][c:16]([Br:17])[cH:18]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[CH:9]([CH2:10][NH2:11])[c:12]2[cH:13][cH:14][cH:15][c:16]([Br:17])[cH:18]2)[cH:19][cH:20]1 | Cc1ccc(S(=O)(=O)Cl)cc1.NCCc1cccc(Br)c1 | Cc1ccc(S(=O)(=O)C(CN)c2cccc(Br)c2)cc1 | null | null | C1CCOC1 | Functional Group Interconversion | OtherReaction | 0cd2ed4c6a94f21490c2adf2b68d468bae5848a2a7182f1ca312bdc9820ddd3f | fcd366d2a12b9f2b1304281b4b55e60873460be0844fd3f482f05b099eb21cf7 | O=S(=O)(Cc1ccccc1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[N;D1;H2:7]-[C:8]-[CH2;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[N;D1;H2:7]-[C:8]-[CH;D3;+0:9](-[c:10](:[c:11]):[c:12])-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | 68.4 | [{"value": 68.4, "product": "BrC=1C=C(C=CC1)C(CN)S(=O)(=O)C1=CC=C(C=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | 3-Bromophenylethylamine hydrochloride (9.44 g) was added to THF (60 ml) containing triethylamine (12.24 ml) and stirred-under argon at 5° C. during the portionwise addition over 15 minutes of 4-methylphenylsulphonyl chloride (11.44 g). The slurry was diluted with THF (50 ml) and stirred for 16 h. The solid was filtered... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Sulfonyl halide | Tosylate | null | null | c1ccccc1.c1ccccc1 | HCl | C1CCOC1 | null | 16 | Cc1ccc(S(=O)(=O)Cl)cc1.NCCc1cccc(Br)c1>C1CCOC1>Cc1ccc(S(=O)(=O)C(CN)c2cccc(Br)c2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-adc4df26b1f04203ac53fb02abc42a4f | NC(=O)Nc1cc(Br)sc1C(N)=O.OB(O)c1cc2ccccc2s1>>NC(=O)Nc1cc(-c2cc3ccccc3s2)sc1C(N)=O | NC(=O)NC1=C(SC(=C1)Br)C(=O)N.S1C(=CC2=C1C=CC=C2)B(O)O>>NC(=O)NC1=C(SC(=C1)C=1SC2=C(C1)C=CC=C2)C(=O)N | Br[c:7]1[cH:6][c:5]([NH:4][C:2]([NH2:1])=[O:3])[c:18]([C:19]([NH2:20])=[O:21])[s:17]1.OB(O)[c:8]1[cH:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[s:16]1>>[NH2:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7](-[c:8]2[cH:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[s:16]2)[s:17][c:18]1[C:19]([NH2:20])=[O:21] | NC(=O)Nc1cc(Br)sc1C(N)=O.OB(O)c1cc2ccccc2s1 | NC(=O)Nc1cc(-c2cc3ccccc3s2)sc1C(N)=O | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 9afab3685eed4a926cff56f3cd0d2eb48abffd401e4ed0c15bf27573a5ca78bf | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1csc(-c2cc3ccccc3s2)c1 | Br-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3](-[C:4](-[N;D1;H2:5])=[O;D1;H0:6]):[c:7]:[c:8]:1.O-B(-O)-[c;H0;D3;+0:9]1:[#16;a:10]:[c:11]:[c:12]:[c:13]:1>>[N;D1;H2:5]-[C:4](=[O;D1;H0:6])-[c:3]1:[#16;a:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:9]2:[#16;a:10]:[c:11]:[c:12]:[c:13]:2):[c:8]:[c:7]:1 | null | [] | null | null | null | null | The title compound was prepared from 3-[(aminocarbonyl)amino-5-bromothiophene-2-carboxamide and 1-benzothien-2-ylboronic acid in a similar manner to Example 11 (g).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccsc1.c1ccc2sccc2c1 | c1ccsc1.c1ccc2sccc2c1 | c1ccsc1.c1ccc2sccc2c1 | HBr.B | null | null | null | NC(=O)Nc1cc(Br)sc1C(N)=O.OB(O)c1cc2ccccc2s1>>NC(=O)Nc1cc(-c2cc3ccccc3s2)sc1C(N)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ec579a0bb64c4ff396c5f146d1122968 | COC(=O)c1ccc(C(=O)[O-])s1.Cc1ccc([C@H](C)N)cc1>>COC(=O)c1ccc(C(=O)N[C@@H](C)c2ccc(C)cc2)s1 | S1C(=CC=C1C(=O)[O-])C(=O)OC.S(=O)(Cl)Cl.C1(=CC=C(C=C1)[C@H](C)N)C.C(C)N(CC)CC>>COC(=O)C=1SC(=CC1)C(N[C@@H](C)C1=CC=C(C=C1)C)=O | [O-][C:9]([c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[s:21]1)=[O:10].[NH2:11][C@@H:12]([CH3:13])[c:14]1[cH:15][cH:16][c:17]([CH3:18])[cH:19][cH:20]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[NH:11][C@@H:12]([CH3:13])[c:14]2[cH:15][cH:16][c:17]([CH3:18])[cH:19][cH:20]2)[s:21]1 | COC(=O)c1ccc(C(=O)[O-])s1.Cc1ccc([C@H](C)N)cc1 | COC(=O)c1ccc(C(=O)N[C@@H](C)c2ccc(C)cc2)s1 | null | CN(C)C=O | C(Cl)Cl | Acylation | OtherReaction | 01b411aa709aa72475efefee2037796aeb41c60940ddba8e15aefc45a95317a8 | 45ca336cc0b18cf59a837ab710e8845f67d23306b24bf1f37b36a34a2de4779a | O=C(NCc1ccccc1)c1cccs1 | [#8:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#16;a:5]:[c:6](-[C;H0;D3;+0:7](-[O-])=[O;D1;H0:8]):[c:9].[C;D1;H3:10]-[C:11](-[NH2;D1;+0:12])-[c:13]>>[#8:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#16;a:5]:[c:6](-[C;H0;D3;+0:7](=[O;D1;H0:8])-[NH;D2;+0:12]-[C:11](-[C;D1;H3:10])-[c:13]):[c:9] | 71 | [{"value": 71.0, "product": "COC(=O)C=1SC(=CC1)C(N[C@@H](C)C1=CC=C(C=C1)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | A solution of 1.4 g (7.5 mmol) of methyl thiophen-2,5-dicarboxylate in CH2Cl2 (5 ml) is treated with 1.5 ml (18 mmol) thionylchloride and one drop of DMF and subsequently heated at 80° C. for 1 hour. The solvent and excess of thionylchloride are evaporated under reduced pressure, and the residue is dissolved in CH2Cl2 ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Secondary amide | null | null | c1ccsc1.c1ccccc1 | HO- | CN(C)C=O.C(Cl)Cl | 80 | null | COC(=O)c1ccc(C(=O)[O-])s1.Cc1ccc([C@H](C)N)cc1>CN(C)C=O.C(Cl)Cl>COC(=O)c1ccc(C(=O)N[C@@H](C)c2ccc(C)cc2)s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dd8830353a284752b61a36e101312188 | CC(N)c1cccs1.COC(=O)c1ccc(C(=O)[O-])s1>>COC(=O)c1ccc(C(=O)NC(C)c2cccs2)s1 | S1C(=CC=C1)C(C)N.S1C(=CC=C1C(=O)[O-])C(=O)OC.O.ON1N=NC2=C1C=CC=C2.Cl.CN(CCCN=C=NCC)C>>COC(=O)C=1SC(=CC1)C(NC(C)C=1SC=CC1)=O | [NH2:11][CH:12]([CH3:13])[c:14]1[cH:15][cH:16][cH:17][s:18]1.[O-][C:9]([c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[s:19]1)=[O:10]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[NH:11][CH:12]([CH3:13])[c:14]2[cH:15][cH:16][cH:17][s:18]2)[s:19]1 | CC(N)c1cccs1.COC(=O)c1ccc(C(=O)[O-])s1 | COC(=O)c1ccc(C(=O)NC(C)c2cccs2)s1 | null | null | C(Cl)Cl | Acylation | OtherReaction | 01b411aa709aa72475efefee2037796aeb41c60940ddba8e15aefc45a95317a8 | 45ca336cc0b18cf59a837ab710e8845f67d23306b24bf1f37b36a34a2de4779a | O=C(NCc1cccs1)c1cccs1 | [#16;a:1]:[c:2]-[C:3](-[C;D1;H3:4])-[NH2;D1;+0:5].[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]:[#16;a:10]:[c:11](-[C;H0;D3;+0:12](-[O-])=[O;D1;H0:13]):[c:14]>>[#16;a:1]:[c:2]-[C:3](-[C;D1;H3:4])-[NH;D2;+0:5]-[C;H0;D3;+0:12](=[O;D1;H0:13])-[c:11](:[c:14]):[#16;a:10]:[c:9]-[C:7](-[#8:6])=[O;D1;H0:8] | 84 | [{"value": 84.0, "product": "COC(=O)C=1SC(=CC1)C(NC(C)C=1SC=CC1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of 500 mg (2.7 mmol) of methyl thiophen-2,5-dicarboxylate in CH2Cl2 (20 ml) is treated with 617 mg (4 mmol) 1-hydroxybenzotriazole hydrate and 772 mg (4 mmol) N′-(3-dimethylaminopropyl)-N-ethylcarbodiimid hydrochloride and stirring is continued at ambient temperature for 1 hour. 410 mg (3.2 mmol) of 1-thioph... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Secondary amide | null | null | c1ccsc1.c1ccsc1 | HO- | C(Cl)Cl | null | 1 | CC(N)c1cccs1.COC(=O)c1ccc(C(=O)[O-])s1>C(Cl)Cl>COC(=O)c1ccc(C(=O)NC(C)c2cccs2)s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0be30f756b24468c9c36d5c24ba0fe57 | CCCCCN.CS(=O)(=O)OCCC12CC3CC(CC(C3)C1)C2>>CCCCCNCCC12CC3CC(CC(C3)C1)C2 | C(CCCC)N.C([O-])([O-])=O.[K+].[K+].[I-].[Na+].CS(=O)(=O)OCCC12CC3CC(CC(C1)C3)C2.Cl>>Cl.C12(CC3CC(CC(C1)C3)C2)CCNCCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][NH2:6].CS(=O)(=O)O[CH2:7][CH2:8][C:9]12[CH2:10][CH:11]3[CH2:12][CH:13]([CH2:14][CH:15]([CH2:16]3)[CH2:17]1)[CH2:18]2>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][CH2:7][CH2:8][C:9]12[CH2:10][CH:11]3[CH2:12][CH:13]([CH2:14][CH:15]([CH2:16]3)[CH2:17]1)[CH2:18]2 | CCCCCN.CS(=O)(=O)OCCC12CC3CC(CC(C3)C1)C2 | CCCCCNCCC12CC3CC(CC(C3)C1)C2 | null | null | C(C)(=O)OCC.C(C)O | Heteroatom Alkylation and Arylation | Alkylation of amines | 8445343b2fb2fd8a9bc06f8532794f2ba6b99565a6e05a3bb9a4344ce2671186 | 7e6303acde8be57b43b4c6a673e1c7537b1efde90f08932e09e153dbba53a700 | C1C2CC3CC1CC(C2)C3 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH2;D1;+0:6]>>[C:4]-[C:5]-[NH;D2;+0:6]-[CH2;D2;+0:1]-[C:2]-[C:3] | null | [] | null | null | null | null | Pentylamine (2.69 ml, 23.2 mmol), potassium carbonate (2.14 g, 15.5 mmol) and sodium iodide (2.30 g, 15.3 mmol) were added to a solution of 2-(1-adamantyl)ethyl methanesulfonate (2.07 g, 8.01 mmol) in ethanol (45.8 ml), and the mixture was refluxed for 17 hours. The reaction mixture was concentrated under reduced press... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Primary amine | Secondary amine | null | null | C1C2CC3CC1CC(C2)C3 | MsOH.HO- | C(C)(=O)OCC.C(C)O | null | null | CCCCCN.CS(=O)(=O)OCCC12CC3CC(CC(C3)C1)C2>C(C)(=O)OCC.C(C)O>CCCCCNCCC12CC3CC(CC(C3)C1)C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-32b25cabc2204a3c84c6a781a1d54418 | O=C1c2ccccc2C(=O)N1CCCc1ccncc1>>NCCCc1ccncc1 | N1=CC=C(C=C1)CCCN1C(C=2C(C1=O)=CC=CC2)=O.O.NN>>NCCCC1=CC=NC=C1 | O=C1c2ccccc2C(=O)[N:1]1[CH2:2][CH2:3][CH2:4][c:5]1[cH:6][cH:7][n:8][cH:9][cH:10]1>>[NH2:1][CH2:2][CH2:3][CH2:4][c:5]1[cH:6][cH:7][n:8][cH:9][cH:10]1 | O=C1c2ccccc2C(=O)N1CCCc1ccncc1 | NCCCc1ccncc1 | null | null | CO | Reduction | Phthalimide deprotection | d9f63cee80ef758bd939ff2a10772447b3092f1576180488281833a98eb1691a | dbfe4201a9328005dfaec4c3f363ddbb4ef3c9b825f648735dc97b2b57396333 | c1ccncc1 | O=C1-[N;H0;D3;+0:1](-[C:2]-[C:3])-C(=O)-c2:c:c:c:c:c:2-1>>[C:3]-[C:2]-[NH2;D1;+0:1] | 60 | [{"value": 60.0, "product": "NCCCC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.7, "product": "NCCCC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | N-[3-(4-Pyridyl)propyl]phthalimide (67.1 g, 252 mmol) was mixed with methanol (504 ml) and hydrazine monohydrate (18.3 ml, 378 mmol), and the mixture was refluxed for three hours. The reaction mixture was allowed to stand, then an insoluble matter was filtered out, and the filtrate was concentrated under reduced pressu... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Primary amine | c1ccc2c(c1)C[NH]C2 | null | c1ccncc1 | HO- | CO | null | null | O=C1c2ccccc2C(=O)N1CCCc1ccncc1>CO>NCCCc1ccncc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-77e4a237654146e5910d99caf230f57d | CNC(=O)CC12CC3CC(CC(C3)C1)C2>>CNCCC12CC3CC(CC(C3)C1)C2 | [H-].[Al+3].[Li+].[H-].[H-].[H-].CNC(CC12CC3CC(CC(C1)C3)C2)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(C)(=O)OCC>>C12(CC3CC(CC(C1)C3)C2)CCNC | O=[C:3]([NH:2][CH3:1])[CH2:4][C:5]12[CH2:6][CH:7]3[CH2:8][CH:9]([CH2:10][CH:11]([CH2:12]3)[CH2:13]1)[CH2:14]2>>[CH3:1][NH:2][CH2:3][CH2:4][C:5]12[CH2:6][CH:7]3[CH2:8][CH:9]([CH2:10][CH:11]([CH2:12]3)[CH2:13]1)[CH2:14]2 | CNC(=O)CC12CC3CC(CC(C3)C1)C2 | CNCCC12CC3CC(CC(C3)C1)C2 | null | null | O1CCCC1.C(C)OCC | Reduction | Reduction of secondary amides to amines | 85b757f1833edc9e5c6365ee6b904683f414e7b9a5f9bfcfd7addca401447058 | ab40188eef2f825df7003af0ffae31d0ce53d126542122535627d3d354cbc9fe | C1C2CC3CC1CC(C2)C3 | O=[C;H0;D3;+0:1](-[#7:2]-[C;D1;H3:3])-[C:4]-[C:5]>>[C:5]-[C:4]-[CH2;D2;+0:1]-[#7:2]-[C;D1;H3:3] | 66 | [{"value": 66.0, "product": "C12(CC3CC(CC(C1)C3)C2)CCNC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.8, "product": "C12(CC3CC(CC(C1)C3)C2)CCNC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 1-adamantaneacetic acid N-methylamide (1.54 g, 7.45 mmol) in tetrahydrofuran (15.0 ml) was added dropwise to a solution of lithium aluminum hydride (569 mg, 15.0 mmol) in diethyl ether (34.0 ml) under ice-cooling over five minutes. The mixture was refluxed for six hours and then stirred under ice-cooling ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | null | null | C1C2CC3CC1CC(C2)C3 | Other | O1CCCC1.C(C)OCC | null | null | CNC(=O)CC12CC3CC(CC(C3)C1)C2>O1CCCC1.C(C)OCC>CNCCC12CC3CC(CC(C3)C1)C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a9db451ed9c34a17965ac9e79daed3a9 | C=CC(=O)OC(C)(C)C.NCCC12CC3CC(CC(C3)C1)C2>>CC(C)(C)OC(=O)CCNCCC12CC3CC(CC(C3)C1)C2 | Cl.C(C)(=O)OCC.C(C)N(CC)CC.C(C=C)(=O)OC(C)(C)C.Cl.C12(CC3CC(CC(C1)C3)C2)CCN>>Cl.C12(CC3CC(CC(C1)C3)C2)CCNCCC(=O)OC(C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH:8]=[CH2:9].[NH2:10][CH2:11][CH2:12][C:13]12[CH2:14][CH:15]3[CH2:16][CH:17]([CH2:18][CH:19]([CH2:20]3)[CH2:21]1)[CH2:22]2>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][CH2:9][NH:10][CH2:11][CH2:12][C:13]12[CH2:14][CH:15]3[CH2:16][CH:17]([CH2:18][CH:19]([CH2:... | C=CC(=O)OC(C)(C)C.NCCC12CC3CC(CC(C3)C1)C2 | CC(C)(C)OC(=O)CCNCCC12CC3CC(CC(C3)C1)C2 | null | null | C(C)O | Heteroatom Alkylation and Arylation | aza-Michael addition primary | 1a11d98577799a07170cd5efd9dd7bb03f34d533a77a248c8322bf305dad4248 | d462df48e06a3b2a50bc83cb7c56b836b8a054b4c300671faa54924b570d58bc | C1C2CC3CC1CC(C2)C3 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[#8:5]-[C:6](=[O;D1;H0:7])-[CH;D2;+0:8]=[CH2;D1;+0:9].[C:10]-[C:11]-[NH2;D1;+0:12]>>[C:10]-[C:11]-[NH;D2;+0:12]-[CH2;D2;+0:9]-[CH2;D2;+0:8]-[C:6](=[O;D1;H0:7])-[#8:5]-[C:2](-[C;D1;H3:1])(-[C;D1;H3:3])-[C;D1;H3:4] | 23 | [{"value": 23.0, "product": "Cl.C12(CC3CC(CC(C1)C3)C2)CCNCCC(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 20.9, "product": "Cl.C12(CC3CC(CC(C1)C3)C2)CCNCCC(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 2-(1-Adamantyl)ethylamine hydrochloride (1.0 g, 4.6 mmol) was dissolved in ethanol (10 ml), and triethylamine (0.65 ml, 4.6 mmol) and t-butyl acrylate (0.75 ml, 5.1 mmol) were added to the solution under ice-cooling. Then, the temperature was raised to room temperature, and the mixture was stirred overnight. The reacti... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine.Vinyl | Ester.Secondary amine | null | null | C1C2CC3CC1CC(C2)C3 | null | C(C)O | null | 8 | C=CC(=O)OC(C)(C)C.NCCC12CC3CC(CC(C3)C1)C2>C(C)O>CC(C)(C)OC(=O)CCNCCC12CC3CC(CC(C3)C1)C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7334d532e9ad4ab796ccc45ccdd76cb0 | CC(C)(C)OC(=O)OC(C)(C)C.O=C(O)CCNCCC1CCCCC1>>CC(C)(C)OC(=O)N(CCC(=O)O)CCC1CCCCC1 | C(CC(O)(C(=O)O)CC(=O)O)(=O)O.Cl.C1(CCCCC1)CCNCCC(=O)O.C(OC(C)(C)C)(OC(C)(C)C)=O.C(C)N(CC)CC>>C(C)(C)(C)OC(=O)N(CCC1CCCCC1)CCC(=O)O | CC(C)(C)O[C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7].[NH:8]([CH2:9][CH2:10][C:11](=[O:12])[OH:13])[CH2:14][CH2:15][CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]([CH2:9][CH2:10][C:11](=[O:12])[OH:13])[CH2:14][CH2:15][CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][C... | CC(C)(C)OC(=O)OC(C)(C)C.O=C(O)CCNCCC1CCCCC1 | CC(C)(C)OC(=O)N(CCC(=O)O)CCC1CCCCC1 | null | null | O1CCCC1 | Protection | Boc amine protection of secondary amine | 4d1c049c3720d7609e462c8feada81a1096592e0829b2b03fa5a358a187681a8 | f0869a0b34976f381b42755ff52efacfde708ff6f8d3c39d434136b4f68fd40e | C1CCCCC1 | C-C(-C)(-C)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-[C:13](=[O;D1;H0:14])-[O;D1;H1:15]>>[C:8]-[C:9]-[N;H0;D3;+0:10](-[C:11]-[C:12]-[C:13](=[O;D1;H0:14])-[O;D1;H1:15])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])... | 62.8 | [{"value": 62.0, "product": "C(C)(C)(C)OC(=O)N(CCC1CCCCC1)CCC(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.8, "product": "C(C)(C)(C)OC(=O)N(CCC1CCCCC1)CCC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Next, tetrahydrofuran (8 ml) was added to 3-[N-(2-cyclohexylethyl)amino]propionic acid hydrochloride (1.0 g, 4.2 mmol), and the mixture was stirred at room temperature. Di-t-butyl carbonate (1.1 g, 5.1 mmol) and triethylamine (1.3 ml, 9.3 mmol) were added to the mixture, the whole was stirred overnight, and then a 5% a... | 10.6084/m9.figshare.5104873.v1 | null | Carbonic Ester.Secondary amine.Boc.Boc | Carbamic ester | null | null | C1CCCCC1 | HO- | O1CCCC1 | null | null | CC(C)(C)OC(=O)OC(C)(C)C.O=C(O)CCNCCC1CCCCC1>O1CCCC1>CC(C)(C)OC(=O)N(CCC(=O)O)CCC1CCCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ce5a3a506d31462fa58328770e3568d0 | CC(C)(C)OC(=O)N(CCC(=O)O)CCC1CCCCC1.N>>CC(C)(C)OC(=O)N(CCC(N)=O)CCC1CCCCC1 | CN1CCOCC1.ClC(=O)OCC(C)C.N.C(C)(C)(C)OC(=O)N(CCC1CCCCC1)CCC(=O)O>>C(C)(C)(C)OC(=O)N(CCC1CCCCC1)CCC(=O)N | O[C:11]([CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:14][CH2:15][CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1)=[O:13].[NH3:12]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]([CH2:9][CH2:10][C:11]([NH2:12])=[O:13])[CH2:14][CH2:15][CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1 | CC(C)(C)OC(=O)N(CCC(=O)O)CCC1CCCCC1.N | CC(C)(C)OC(=O)N(CCC(N)=O)CCC1CCCCC1 | null | null | C(Cl)(Cl)Cl.O1CCCC1 | Acylation | Carboxylic acid to amide conversion | 1283aef55d7ee699f097a8e5267689198c76ba671644401547f902657820236d | cb0a71c3fb37a76e96fbd81aae6f95a28398a03d1ad2c8e877085e735efb98f1 | C1CCCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH3;D0;+0:5]>>[C:4]-[C:3]-[C;H0;D3;+0:1](-[NH2;D1;+0:5])=[O;D1;H0:2] | 58 | [{"value": 58.0, "product": "C(C)(C)(C)OC(=O)N(CCC1CCCCC1)CCC(=O)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.0, "product": "C(C)(C)(C)OC(=O)N(CCC1CCCCC1)CCC(=O)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 1 | HOUR | Next, anhydrous tetrahydrofuran (7 ml) was added to 3-[N-(t-butoxycarbonyl)-N-(2-cyclohexylethyl)amino]propionic acid (0.59 g, 2.0 mmol), and the mixture was stirred at −78° C. N-Methylmorpholine (0.22 ml, 2.0 mmol) and then a solution of isobutyl chloroformate (0.38 ml, 2.9 mmol) in tetrahydrofuran (3 ml) were added t... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary amide | null | null | C1CCCCC1 | HO- | C(Cl)(Cl)Cl.O1CCCC1 | -78 | 1 | CC(C)(C)OC(=O)N(CCC(=O)O)CCC1CCCCC1.N>C(Cl)(Cl)Cl.O1CCCC1>CC(C)(C)OC(=O)N(CCC(N)=O)CCC1CCCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-58a7af91c94048528b7c9e20557128a1 | CC(C)(C)OC(=O)N(CCC(N)=O)CCC1CCCCC1>>NC(=O)CCNCCC1CCCCC1 | Cl.C(C)(C)(C)OC(=O)N(CCC1CCCCC1)CCC(=O)N>>Cl.C1(CCCCC1)CCNCCC(=O)N | CC(C)(C)OC(=O)[N:7]([CH2:6][CH2:5][C:3]([NH2:2])=[O:4])[CH2:8][CH2:9][CH:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1>>[NH2:2][C:3](=[O:4])[CH2:5][CH2:6][NH:7][CH2:8][CH2:9][CH:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1 | CC(C)(C)OC(=O)N(CCC(N)=O)CCC1CCCCC1 | NC(=O)CCNCCC1CCCCC1 | null | null | O1CCOCC1 | Reduction | Boc amine deprotection | bbda4640db5f48af4538caded12fdadd56eacd6d4e5f7aefe46282d665df167e | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | C1CCCCC1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3]-[C:4](-[N;D1;H2:5])=[O;D1;H0:6])-[C:7]-[C:8]>>[C:8]-[C:7]-[NH;D2;+0:1]-[C:2]-[C:3]-[C:4](-[N;D1;H2:5])=[O;D1;H0:6] | null | [] | null | null | 8 | HOUR | Next, a 4 N solution of hydrogen chloride in 1,4-dioxane (3.1 ml) was added to 3-[N-(t-butoxycarbonyl)-N-(2-cyclohexylethyl)amino]propionamide (0.37 g, 1.2 mmol), and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, diisopropyl ether was added to the r... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | null | null | C1CCCCC1 | HO- | O1CCOCC1 | null | 8 | CC(C)(C)OC(=O)N(CCC(N)=O)CCC1CCCCC1>O1CCOCC1>NC(=O)CCNCCC1CCCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5be7de404eea4fd0bdb5fb8ce7e9a3b1 | C=CCCCCBr.N#CCCN>>C=CCCCCN(CCC#N)CCCCC=C | NCCC#N.BrCCCCC=C.[I-].[Na+].C([O-])([O-])=O.[K+].[K+]>>C(CCCC=C)N(CCC#N)CCCCC=C | Br[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=[CH2:1].[NH2:7][CH2:8][CH2:9][C:10]#[N:11]>>[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]([CH2:8][CH2:9][C:10]#[N:11])[CH2:12][CH2:13][CH2:14][CH2:15][CH:16]=[CH2:17] | C=CCCCCBr.N#CCCN | C=CCCCCN(CCC#N)CCCCC=C | null | null | CN(C=O)C.C(C)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 893159deb190bcd5d94ea1ac88545c2b9efcc6fe5a877afc78c45c79762aed30 | 0322f1bef343d356b182167b04cb498d47c01a8d0a957f61ec7a913a1a731a73 | null | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH2;D1;+0:6]>>[C:7]-[C:8]-[N;H0;D3;+0:6](-[C:5]-[C:4])-[CH2;D2;+0:1]-[C:2]-[C:3] | 67 | [{"value": 66.0, "product": "C(CCCC=C)N(CCC#N)CCCCC=C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.0, "product": "C(CCCC=C)N(CCC#N)CCCCC=C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | N,N-Dimethylformamide (28 ml) was added to 3-aminopropionitrile (0.98 g, 14 mmol), and the mixture was stirred at room temperature. 6-Bromo-1-hexene (5.0 g, 31 mmol), sodium iodide (11 g, 73 mmol) and potassium carbonate (5.8 g, 42 mmol) were added to the mixture, and the whole was stirred overnight. The reaction mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Tertiary amine.Allyl | null | null | null | Br- | CN(C=O)C.C(C)OCC | null | null | C=CCCCCBr.N#CCCN>CN(C=O)C.C(C)OCC>C=CCCCCN(CCC#N)CCCCC=C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9e54ec4ad8e845f3b4b1b6c76d7c398a | C=CCCCCN(CCC#N)CCCCC=C>>C=CCCCCNCCCCC=C | C(C)O.[OH-].[K+].C(CCCC=C)N(CCC#N)CCCCC=C.O>>C(CCCC=C)NCCCCC=C | N#CCC[N:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=[CH2:1])[CH2:8][CH2:9][CH2:10][CH2:11][CH:12]=[CH2:13]>>[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][NH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]=[CH2:13] | C=CCCCCN(CCC#N)CCCCC=C | C=CCCCCNCCCCC=C | null | null | C(Cl)(Cl)Cl | Deprotection | Hydrogenolysis of tertiary amines | 4b6010e5e556cbe56e0a23d77d5f962bf217f63ee41103fbe0dcec4149aedd5d | a30cc707bf4c7b9b99c27f4acdf47f0e8bad9208c92eb9e63ca05b9b9a8bb677 | null | N#C-C-C-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5] | 21 | [{"value": 21.0, "product": "C(CCCC=C)NCCCCC=C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 20.5, "product": "C(CCCC=C)NCCCCC=C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Next, ethanol (8.6 ml) and potassium hydroxide (0.85 g, 13 mmol) were added to 3-(di-5-hexenyl)aminopropionitrile (2.0 g, 8.6 mmol), and the mixture was refluxed for 7.5 hours. The reaction mixture was allowed to stand, and then water (150 ml) and chloroform (150 ml) were added to the reaction mixture. Layers were sepa... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Tertiary amine | Secondary amine | null | null | null | Other | C(Cl)(Cl)Cl | null | null | C=CCCCCN(CCC#N)CCCCC=C>C(Cl)(Cl)Cl>C=CCCCCNCCCCC=C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6b443fee26bd4e5cba1adb728c7a6abc | CC(C)(C)OC(=O)OC(C)(C)C.CCCN.O=C(O)CBr>>CCCN(CC(=O)O)C(=O)OC(C)(C)C | BrCC(=O)O.C(CC)N.C(OC(C)(C)C)(OC(C)(C)C)=O.O.C(CC(O)(C(=O)O)CC(=O)O)(=O)O.[OH-].[Na+]>>C(C)(C)(C)OC(=O)N(CCC)CC(=O)O | CC(C)(C)O[C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15].[CH3:1][CH2:2][CH2:3][NH2:4].Br[CH2:5][C:6](=[O:7])[OH:8]>>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][C:6](=[O:7])[OH:8])[C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15] | CC(C)(C)OC(=O)OC(C)(C)C.CCCN.O=C(O)CBr | CCCN(CC(=O)O)C(=O)OC(C)(C)C | null | null | O1CCCC1.C(C)O | Protection | OtherReaction | 8aca72de400b3fa0782c5a378792f827b46acc3e8d97562410d465678077336b | 7138c285dc4ea6808ea170128b99c537f34ab199796eadcb94992b3f39be8247 | null | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[O;D1;H1:4].C-C(-C)(-C)-O-[C;H0;D3;+0:5](=[O;D1;H0:6])-[#8:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11].[C:12]-[C:13]-[NH2;D1;+0:14]>>[C:12]-[C:13]-[N;H0;D3;+0:14](-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[O;D1;H1:4])-[C;H0;D3;+0:5](=[O;D1;H0:6])-[#8:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3... | 65 | [{"value": 65.0, "product": "C(C)(C)(C)OC(=O)N(CCC)CC(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.7, "product": "C(C)(C)(C)OC(=O)N(CCC)CC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | Ethanol (36 ml) was added to bromoacetic acid (5.00 g, 36.0 mmol), and the mixture was stirred under ice-cold water-cooling. Propylamine (14.8 ml, 180 mmol) was added to the mixture over one minute, and then the whole was stirred at an external temperature of 80° C. for 2.5 hours. A 4 N aqueous sodium hydroxide solutio... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carbonic Ester.Primary amine.Boc.Boc | Carbamic ester.Ether.Boc | null | null | null | HBr | O1CCCC1.C(C)O | null | 0.25 | CC(C)(C)OC(=O)OC(C)(C)C.CCCN.O=C(O)CBr>O1CCCC1.C(C)O>CCCN(CC(=O)O)C(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-352b45ba8a4c4cccbe141dd427679355 | CCCN(CC(=O)O)C(=O)OC(C)(C)C.NC12CC3CC(CC(C3)C1)C2>>CCCN(CC(=O)NC12CC3CC(CC(C3)C1)C2)C(=O)OC(C)(C)C | C(C)(C)(C)OC(=O)N(CCC)CC(=O)O.C12(CC3CC(CC(C1)C3)C2)N.C(C)(C)N(C(C)C)CC>>C12(CC3CC(CC(C1)C3)C2)NC(CN(CCC)C(=O)OC(C)(C)C)=O | O[C:6]([CH2:5][N:4]([CH2:3][CH2:2][CH3:1])[C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:7].[NH2:8][C:9]12[CH2:10][CH:11]3[CH2:12][CH:13]([CH2:14][CH:15]([CH2:16]3)[CH2:17]1)[CH2:18]2>>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][C:6](=[O:7])[NH:8][C:9]12[CH2:10][CH:11]3[CH2:12][CH:13]([CH2:14][CH:15]([CH2:16]3)[CH2... | CCCN(CC(=O)O)C(=O)OC(C)(C)C.NC12CC3CC(CC(C3)C1)C2 | CCCN(CC(=O)NC12CC3CC(CC(C3)C1)C2)C(=O)OC(C)(C)C | null | null | C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | C1C2CC3CC1CC(C2)C3 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11].[C:12]-[C:13](-[NH2;D1;+0:14])(-[C:15])-[C:16]>>[C:12]-[C:13](-[NH;D2;+0:14]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11])(-[C:15... | null | [] | null | null | null | null | Next, methylene chloride (208 ml) was added to a mixture of 2-[N-(t-butoxycarbonyl)-N-propylamino]acetic acid (4.52 g, 20.8 mmol) and 1-adamantaneamine (3.46 g, 22.9 mmol), and the whole was stirred at room temperature. N,N-Diisopropylethylamine (7.25 ml, 41.6 mmol) and then O-(7-azabenzotriazol-1-yl)-N,N,N′,N-tetramet... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1C2CC3CC1CC(C2)C3 | HO- | C(Cl)Cl | null | null | CCCN(CC(=O)O)C(=O)OC(C)(C)C.NC12CC3CC(CC(C3)C1)C2>C(Cl)Cl>CCCN(CC(=O)NC12CC3CC(CC(C3)C1)C2)C(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-11ce434220d74253ad122a096065b5d9 | CCCN(CC(=O)NC12CC3CC(CC(C3)C1)C2)C(=O)OC(C)(C)C>>CCCNCC(=O)NC12CC3CC(CC(C3)C1)C2 | Cl.C(C)(=O)OCC.C12(CC3CC(CC(C1)C3)C2)NC(CN(CCC)C(=O)OC(C)(C)C)=O>>C12(CC3CC(CC(C1)C3)C2)NC(CNCCC)=O | CC(C)(C)OC(=O)[N:4]([CH2:3][CH2:2][CH3:1])[CH2:5][C:6](=[O:7])[NH:8][C:9]12[CH2:10][CH:11]3[CH2:12][CH:13]([CH2:14][CH:15]([CH2:16]3)[CH2:17]1)[CH2:18]2>>[CH3:1][CH2:2][CH2:3][NH:4][CH2:5][C:6](=[O:7])[NH:8][C:9]12[CH2:10][CH:11]3[CH2:12][CH:13]([CH2:14][CH:15]([CH2:16]3)[CH2:17]1)[CH2:18]2 | CCCN(CC(=O)NC12CC3CC(CC(C3)C1)C2)C(=O)OC(C)(C)C | CCCNCC(=O)NC12CC3CC(CC(C3)C1)C2 | null | null | null | Reduction | Boc amine deprotection | bbda4640db5f48af4538caded12fdadd56eacd6d4e5f7aefe46282d665df167e | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | C1C2CC3CC1CC(C2)C3 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5](=[O;D1;H0:6])-[#7:7]-[C:8]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5](=[O;D1;H0:6])-[#7:7]-[C:8] | 108.9 | [{"value": 95.0, "product": "C12(CC3CC(CC(C1)C3)C2)NC(CNCCC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 108.9, "product": "C12(CC3CC(CC(C1)C3)C2)NC(CNCCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Next, a 4 N solution of hydrogen chloride in ethyl acetate (55 ml, 0.22 mol) was added to 2-[N′(t-butoxycarbonyl)-N-propylamino]acetic acid N-(1-adamantyl)amide (7.68 g, 21.9 mmol), and the mixture was stirred at room temperature for one hour. The resulting crystals were filtered off with ethyl acetate and washed with ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | null | null | C1C2CC3CC1CC(C2)C3 | HO- | null | null | 1 | CCCN(CC(=O)NC12CC3CC(CC(C3)C1)C2)C(=O)OC(C)(C)C>>CCCNCC(=O)NC12CC3CC(CC(C3)C1)C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f6144ee0e8f24ce288490dbd6a6d4c57 | CCOC(=O)C(C)(Cc1ccncc1)C(=O)OCC>>CC(Cc1ccncc1)C(=O)O | Cl.CC(C(=O)OCC)(C(=O)OCC)CC1=CC=NC=C1>>CC(C(=O)O)CC1=CC=NC=C1 | CCOC(=O)[C:2]([CH3:1])([CH2:3][c:4]1[cH:5][cH:6][n:7][cH:8][cH:9]1)[C:10](=[O:11])[O:12]CC>>[CH3:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][n:7][cH:8][cH:9]1)[C:10](=[O:11])[OH:12] | CCOC(=O)C(C)(Cc1ccncc1)C(=O)OCC | CC(Cc1ccncc1)C(=O)O | null | null | null | Reduction | OtherReaction | 5ba27bafcd96d74a94be636caed9361c02821d71f9ddac00396de4e018da642b | 6d9edf77f3bf4688cdf5f5c3ccf062016b04f2e19a67399a3ca7c7e8d575cc5a | c1ccncc1 | C-C-O-C(=O)-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[C:3]-[c:4])-[C:5](=[O;D1;H0:6])-[O;H0;D2;+0:7]-C-C>>[C;D1;H3:2]-[CH;D3;+0:1](-[C:3]-[c:4])-[C:5](=[O;D1;H0:6])-[OH;D1;+0:7] | 100.3 | [{"value": 82.0, "product": "CC(C(=O)O)CC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 100.3, "product": "CC(C(=O)O)CC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Next, 6 N hydrochloric acid (96.8 ml, 581 mmol) was added to diethyl 2-methyl-2-(4-pyridylmethyl)malonate (17.2 g, 64.6 mmol), and the mixture was refluxed overnight. The reaction mixture was allowed to stand, then washed with hexane (100 ml) to remove sodium hydride oil contained in diethyl 2-methyl-2-(4-pyridylmethyl... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Carboxylic acid | null | null | c1ccncc1 | HO- | null | null | null | CCOC(=O)C(C)(Cc1ccncc1)C(=O)OCC>>CC(Cc1ccncc1)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d49184065b21412f8461ac42d39e516f | CC(Cc1ccncc1)C(N)=O>>CC(CN)Cc1ccncc1 | [OH-].[Na+].CC(C(=O)N)CC1=CC=NC=C1.C(C)OCC.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>CC(CN)CC1=CC=NC=C1 | O=[C:3]([CH:2]([CH3:1])[CH2:5][c:6]1[cH:7][cH:8][n:9][cH:10][cH:11]1)[NH2:4]>>[CH3:1][CH:2]([CH2:3][NH2:4])[CH2:5][c:6]1[cH:7][cH:8][n:9][cH:10][cH:11]1 | CC(Cc1ccncc1)C(N)=O | CC(CN)Cc1ccncc1 | null | null | C(C)(=O)OCC.C(Cl)Cl | Reduction | Reduction of primary amides to amines | 71f4ab6e4ff9fd6ad8fb6a6879cdc6c258d35bb85b9b40ad2783b874bf909ba4 | 8776a0c3e2f32dafe87200a597cd55df0b01414bf133bdc9f8f7e1171014bfad | c1ccncc1 | O=[C;H0;D3;+0:1](-[N;D1;H2:2])-[C:3](-[C:4])-[C;D1;H3:5]>>[C:4]-[C:3](-[C;D1;H3:5])-[CH2;D2;+0:1]-[N;D1;H2:2] | 90.9 | [{"value": 90.0, "product": "CC(CN)CC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.9, "product": "CC(CN)CC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Next, anhydrous diethyl ether (20 ml) was added to lithium aluminum hydride (0.45 g, 12 mmol) under a nitrogen atmosphere, and the mixture was stirred under ice-cooling. A solution of 2-methyl-3-(4-pyridyl)propionamide (0.68 g, 4.1 mmol) in anhydrous methylene chloride (20 ml) was added dropwise to the mixture over fiv... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide | null | null | null | c1ccncc1 | Other | C(C)(=O)OCC.C(Cl)Cl | null | null | CC(Cc1ccncc1)C(N)=O>C(C)(=O)OCC.C(Cl)Cl>CC(CN)Cc1ccncc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ee887c7a58eb4662b376f2c9813f3867 | NCC=Cc1ccnc2ccccc12>>NCCCc1ccnc2ccccc12 | N1=CC=C(C2=CC=CC=C12)C=CCN>>N1=CC=C(C2=CC=CC=C12)CCCN | [NH2:1][CH2:2][CH:3]=[CH:4][c:5]1[cH:6][cH:7][n:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]12>>[NH2:1][CH2:2][CH2:3][CH2:4][c:5]1[cH:6][cH:7][n:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]12 | NCC=Cc1ccnc2ccccc12 | NCCCc1ccnc2ccccc12 | null | [Pd] | CO | Reduction | Hydrogenation (double to single) | 0bc3968b35f0839c230afb4215314da278abd4e1f10e42ec3012c5512de49ea5 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | c1ccc2ncccc2c1 | [N;D1;H2:1]-[C:2]-[CH;D2;+0:3]=[CH;D2;+0:4]-[c:5]1:[c:6]:[c:7]:[#7;a:8]:[c:9]:[c:10]:1>>[N;D1;H2:1]-[C:2]-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[c:5]1:[c:6]:[c:7]:[#7;a:8]:[c:9]:[c:10]:1 | 76.3 | [{"value": 76.3, "product": "N1=CC=C(C2=CC=CC=C12)CCCN", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.3, "product": "N1=CC=C(C2=CC=CC=C12)CCCN", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A catalytic amount of 10% palladium on carbon was added to a solution of 3-(4-quinolyl)-2-propenylamine (Intermediate No. 2-4) (188 mg, 1.02 mmol) obtained in Preparation Example 2 in methanol (3 ml) at room temperature under a nitrogen atmosphere, and the mixture was stirred under a hydrogen atmosphere overnight. The ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccc2ncccc2c1 | null | [Pd].CO | null | 8 | NCC=Cc1ccnc2ccccc12>[Pd].CO>NCCCc1ccnc2ccccc12 |
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